Novel 5-substituted imidazolylmethyloxirane derivatives

ABSTRACT

Novel 5-substituted imidazolylmethyloxirane derivatives The present invention relates to novel 5-substituted imidazolylmethyloxirane derivatives, to processes for preparing these compounds, to compositions and mixtures comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.

The present invention relates to novel 5-substitutedimidazolylmethyloxirane derivatives, to processes for preparing thesecompounds, to compositions comprising these compounds, and to the usethereof as biologically active compounds, especially for control ofharmful microorganisms in crop protection and in the protection ofmaterials and as plant growth regulators.

It is already known that imidazole derivatives, which may be substitutedat the imidazole ring, and salts thereof can be used in crop protectionas fungicides, safeners and/or plant growth regulators (cf. e.g. WO-A2013/076228, U.S. Pat. No. 4,085,209, WO-A 2014/118170, EP-A 2 746 259,U.S. Pat. Nos. 4,118,461, 4,115,578, DE-A 2604047, DE-A 2750031, Manabe,Akio; Kirino, Osamu; Funaki, Yuji; Hisada, Yoshio; Takano, Hirotaka;Tanaka, Shizuya, Agricultural and Biological Chemistry (1986), 50(12),3215-17, JP-A 60069067, EP-A 0 130 366, NL-A 8201572, DE-A 2935452, andDE-A 2732750). Moreover, WO-A 2010/089353, EP-A 0421125, DE-A 3930166,EP-A 0388871, EP-A 0386557, DE-A 3825586, EP-A 0332073, DE-A 3737888,Journal of Heterocyclic Chemistry (1988), 25(5), 1439-41, EP-A 0196038,DE-A 3511411, DE-A 3218129 and DE-A 3218130 disclose certainimidazolylmethyloxirane derivatives which are useful as fungicides,herbicides, plant growth regulators and/or in the pharmaceutical area.

Since the ecological and economic demands made on modem activeingredients, for example fungicides, are increasing constantly, forexample with respect to activity spectrum, toxicity, selectivity,application rate, formation of residues and favourable manufacture, andthere can also be problems, for example, with resistances, there is aconstant need to develop novel fungicidal compounds and compositionswhich have advantages over the known compounds and compositions at leastin some areas.

Accordingly, the present invention provides novel compounds of formula(I)

-   wherein-   R¹ and R^(1a) independently from each other represent hydrogen,    C₁-C₅-alkyl, C₁-C₈-haloalkyl, optionally halogen, C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl, optionally halogen,    C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted bicycloalkyl,    optionally halogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl-C₁-C₄-alkyl, optionally C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-halocycloalkyl-C₁-C₄-alkyl,    optionally C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-halocycloalkyl-C₁-C₄-haloalkyl, optionally C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₁-C₄-haloalkyl,    optionally halogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl,    -   naphthyl, 5-membered heteroaryl, or a substituent of formula Q¹,    -   wherein the naphthyl, and 5-membered heteroaryl is        non-substituted or substituted by one or more group(s) selected        from halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms,        C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy        having 1 to 5 halogen atoms, C₃-C₆-cycloalkoxy,        C₁-C₈-alkylsulfonyl, tri(C₁-C₈-alkyl)-silyloxy,        tri(C₁-C₈-alkyl)-silyl, aryl, aryloxy, heteroaryl,        heteroaryloxy,    -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,        tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,        C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,        C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl,        C₁-C₈-alkylsulfonyloxy, C₁-C₈-haloalkylsulfonyloxy, benzyl,        phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered        heteroaryloxy, benzyloxy, or phenyloxy,    -   wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered        heteroaryl, 6-membered heteroaryloxy, benzyloxy, or phenyloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, nitro, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and    -   wherein Q¹ represents a 6-membered aromatic cycle of formula        (Q¹-I)

-   -   wherein    -   U¹ represents CX¹ or N;    -   U² represents CX² or N;    -   U³ represents CX³ or N;    -   U⁴ represents CX⁴ or N;    -   U⁵ represents CX⁵ or N;        -   wherein X¹, X², X³, X⁴, and X⁵ independently from each other            represent hydrogen, halogen, nitro, pentafluoro-λ⁶-sulfanyl,            C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 5 halogen atoms,            C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl having 1 to 5 halogen            atoms, C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy,            C₁-C₈-haloalkoxy having 1 to 5 halogen atoms,            C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfonyl,            tri(C₁-C₈-alkyl)-silyloxy, tri(C₁-C₈-alkyl)-silyl, aryl,            aryloxy, heteroaryl, heteroaryloxy,        -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is            non-substituted or substituted by one or more group(s)            selected from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,            C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,            tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,            C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,            C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl,            C₁-C₈-alkylsulfonyloxy, C₁-C₈-haloalkylsulfonyloxy, benzyl,            phenyl, 5-membered heteroaryl, 6-membered heteroaryl,            6-membered heteroaryloxy, benzyloxy, or phenyloxy,        -   wherein the benzyl, phenyl, 5-membered heteroaryl,            6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy,            or phenyloxy is non-substituted or substituted by one or            more group(s) selected from halogen, nitro, C₁-C₈-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or            pentafluoro-λ⁶-sulfanyl;        -   and wherein at most two of U¹, U², U³, U⁴ and U⁵ can            represent N;        -   or        -   U¹ and U² or U² and U³ or U³ and U⁴ form together an            additional saturated or unsaturated 4 to 6-membered halogen-            or C₁-C₈-alkyl-substituted or non-substituted ring;

-   R² represents C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen,    C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl,    optionally halogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    bicycloalkyl, optionally halogen, C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₁-C₄-alkyl, optionally    C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-halocycloalkyl-C₁-C₄-alkyl, optionally C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-halocycloalkyl-C₁-C₄-haloalkyl,    optionally C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl-C₁-C₄-haloalkyl, optionally halogen, C₁-C₄-alkyl-,    or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl,    -   naphthyl, 5-membered heteroaryl, or a substituent of formula Q²,    -   wherein the naphthyl, and 5-membered heteroaryl is        non-substituted or substituted by one or more group(s) selected        from halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms,        C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy        having 1 to 5 halogen atoms, C₃-C₆-cycloalkoxy,        C₁-C₈-alkylsulfonyl, tri(C₁-C₈-alkyl)-silyloxy,        tri(C₁-C₈-alkyl)-silyl, aryl, aryloxy, heteroaryl,        heteroaryloxy,    -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,        tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,        C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,        C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl,        C₁-C₈-alkylsulfonyloxy, C₁-C₈-haloalkylsulfonyloxy, benzyl,        phenyl, 5-membered heteroaryl, 6-membered heteroaryl, 6-membered        heteroaryloxy, benzyloxy, or phenyloxy,    -   wherein the benzyl, phenyl, 5-membered heteroaryl, 6-membered        heteroaryl, 6-membered heteroaryloxy, benzyloxy, or phenyloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, nitro, C₁-C₅-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,        C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and    -   wherein Q² represents a 6-membered aromatic cycle of formula        (Q²-I)

-   -   wherein    -   Z¹ represents CY¹ or N;    -   Z² represents CY² or N;    -   Z³ represents CY³ or N;    -   Z⁴ represents CY⁴ or N;    -   Z⁵ represents CY⁵ or N;        -   wherein Y¹, Y², Y³, Y⁴, and Y⁵ independently from each other            represent hydrogen, halogen, nitro, pentafluoro-λ⁶-sulfanyl,            C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 5 halogen atoms,            C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl having 1 to 5 halogen            atoms, C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy,            C₁-C₈-haloalkoxy having 1 to 5 halogen atoms,            C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfonyl,            tri(C₁-C₈-alkyl)-silyloxy, tri(C₁-C₈-alkyl)-silyl, aryl,            aryloxy, heteroaryl, heteroaryloxy,        -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is            non-substituted or substituted by one or more group(s)            selected from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,            C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,            tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,            C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,            C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl,            C₁-C₈-alkylsulfonyloxy, C₁-C₈-haloalkylsulfonyloxy, benzyl,            phenyl, 5-membered heteroaryl, 6-membered heteroaryl,            6-membered heteroaryloxy, benzyloxy, or phenyloxy,        -   wherein the benzyl, phenyl, 5-membered heteroaryl,            6-membered heteroaryl, 6-membered heteroaryloxy, benzyloxy,            or phenyloxy is non-substituted or substituted by one or            more group(s) selected from halogen, nitro, C₁-C₈-alkyl,            C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy or            pentafluoro-λ⁶-sulfanyl;        -   and wherein at most two of Z¹, Z², Z³, Z⁴ and Z⁵ can            represent N;        -   or        -   Z¹ and Z² or Z² and Z³ or Z³ and Z⁴ form together an            additional saturated or unsaturated 4 to 6-membered halogen-            or C₁-C₈-alkyl-substituted or non-substituted ring;

-   R³ represents halogen, hydroxyl, cyano, isocyano, amino, sulfanyl,    pentafluoro-λ⁶-sulfanyl, carboxaldehyde, hydroxycarbonyl,    C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-cyanoalkyl, C₁-C₈-alkyloxy,    C₁-C₈-haloalkyloxy, tri(C₁-C₈-alkyl)silyl,    tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₃-C₇-cycloalkyl,    C₃-C₇-halocycloalkyl, C₃-C₇-cycloalkenyl, C₃-C₇-halocycloalkenyl,    C₄-C₁₀-cycloalkylalkyl, C₄-C₁₀-halocycloalkylalkyl,    C₆-C₁₂-cycloalkylcycloalkyl, C₁-C₈-alkyl-C₃-C₇-cycloalkyl,    C₁-C₈-alkoxy-C₃-C₇-cycloalkyl,    tri(C₁-C₈-alkyl)silyl-C₃-C₇-cycloalkyl, C₂-C₈-alkenyl,    C₂-C₈-alkynyl, C₂-C₈-alkenyloxy, C₂-C₈-haloalkenyloxy,    C₃-C₈-alkynyloxy, C₃-C₈-haloalkynyloxy, C₁-C₈-alkylamino,    C₁-C₈-haloalkylamino, C₁-C₈-cyanoalkoxy, C₄-C₈-cycloalkylalkoxy,    C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfanyl, C₁-C₈-haloalkylsulfanyl,    C₁-C₈-alkylcarbonyl, C₁-C₈-haloalkylcarbonyl, arylcarbonyl,    aryl-C₁-C₆-alkylcarbonyl, C₃-C₈-cycloalkylcarbonyl,    C₃-C₈-halocycloalkylcarbonyl, C₁-C₈-alkylcarbamoyl,    di-C₁-C₈-alkylcarbamoyl, N—C₁-C₈-alkyloxycarbamoyl,    C₁-C₈-alkoxycarbamoyl, N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl,    aminothiocarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-haloalkoxycarbonyl,    C₃-C₈-cycloalkoxycarbonyl, C₂-C₈-alkoxyalkylcarbonyl,    C₂-C₈-haloalkoxyalkylcarbonyl, C₃-C₁₀-cycloalkoxyalkylcarbonyl,    C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl,    C₃-C₈-cycloalkylaminocarbonyl, C₁-C₈-alkylcarbonyloxy,    C₁-C₈-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy,    C₁-C₈-alkylcarbonylamino, C₁-C₈-haloalkylcarbonylamino,    C₁-C₈-alkylaminocarbonyloxy, di-C₁-C₈-alkylaminocarbonyloxy,    C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulfinyl,    C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl,    C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,    C₁-C₈-haloalkylsulfonyloxy, C₁-C₈-alkylaminosulfamoyl,    di-C₁-C₈-alkylaminosulfamoyl, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,    (C₃-C₇-cycloalkoxyimino)-C₁-C₈-alkyl, hydroxyimino-C₁-C₈-alkyl,    (C₁-C₈-alkoxyimino)-C₃-C₇-cycloalkyl, hydroxyimino-C₃-C₇-cycloalkyl,    (C₁-C₈-alkylimino)-oxy, (C₁-C₈-alkylimino)-oxy-C₁-C₈-alkyl,    (C₃-C₇-cycloalkylimino)-oxy-C₁-C₈-alkyl,    (C₁-C₆-alkylimino)-oxy-C₃-C₇-cycloalkyl,    (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,    (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, (benzyloxyimino)-C₁-C₈-alkyl,    C₁-C₈-alkoxyalkyl, C₁-C₈-alkylthioalkyl, C₁-C₈-alkoxyalkoxyalkyl,    C₁-C₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl,    6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl,    benzylamino, phenylsulfanyl, or phenylamino, wherein the benzyl,    phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or    phenyloxy is non-substituted or substituted by one or more group(s)    selected from halogen, hydroxyl, cyano, isocyano, amino, sulfanyl,    pentafluoro-λ⁶-sulfanyl, carboxaldehyde, hydroxycarbonyl,    C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-cyanoalkyl, C₁-C₈-alkyloxy,    C₁-C₈-haloalkyloxy, tri(C₁-C₈-alkyl)silyl,    tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₃-C₇-cycloalkyl,    C₃-C₇-halocycloalkyl, C₃-C₇-cycloalkenyl, C₃-C₇-halocycloalkenyl,    C₄-C₁₀-cycloalkylalkyl, C₄-C₁₀-halocycloalkylalkyl,    C₆-C₁₂-cycloalkylcycloalkyl, C₁-C₈-alkyl-C₃-C₇-cycloalkyl,    C₁-C₈-alkoxy-C₃-C₇-cycloalkyl,    tri(C₁-C₈-alkyl)silyl-C₃-C₇-cycloalkyl, C₂-C₈-alkenyl,    C₂-C₈-alkynyl, C₂-C₈-alkenyloxy, C₂-C₈-haloalkenyloxy,    C₃-C₈-alkynyloxy, C₃-C₈-haloalkynyloxy, C₁-C₈-alkylamino,    C₁-C₈-haloalkylamino, C₁-C₈-cyanoalkoxy, C₄-C₈-cycloalkylalkoxy,    C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfanyl, C₁-C₈-haloalkylsulfanyl,    C₁-C₈-alkylcarbonyl, C₁-C₈-haloalkylcarbonyl, arylcarbonyl,    aryl-C₁-C₆-alkylcarbonyl, C₃-C₅-cycloalkylcarbonyl,    C₃-C₈-halocycloalkylcarbonyl, C₁-C₈-alkylcarbamoyl,    di-C₁-C₈-alkylcarbamoyl, N—C₁-C₈-alkyloxycarbamoyl,    C₁-C₈-alkoxycarbamoyl, N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl,    aminothiocarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-haloalkoxycarbonyl,    C₃-C₈-cycloalkoxycarbonyl, C₂-C₈-alkoxyalkylcarbonyl,    C₂-C₈-haloalkoxyalkylcarbonyl, C₃-C₁₀-cycloalkoxyalkylcarbonyl,    C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl,    C₃-C₈-cycloalkylaminocarbonyl, C₁-C₈-alkylcarbonyloxy,    C₁-C₈-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy,    C₁-C₈-alkylcarbonylamino, C₁-C₈-haloalkylcarbonylamino,    C₁-C₈-alkylaminocarbonyloxy, di-C₁-C₈-alkylaminocarbonyloxy,    C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulfinyl,    C₁-C₈-haloalkylsulfinyl, C₁-C₈-alkylsulfonyl,    C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,    C₁-C₈-haloalkylsulfonyloxy, C₁-C₈-alkylaminosulfamoyl,    di-C₁-C₈-alkylaminosulfamoyl, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,    (C₃-C₇-cycloalkoxyimino)-C₁-C₈-alkyl, hydroxyimino-C₁-C₈-alkyl,    (C₁-C₈-alkoxyimino)-C₃-C₇-cycloalkyl, hydroxyimino-C₃-C₇-cycloalkyl,    (C₁-C₈-alkylimino)-oxy, (C₁-C₈-alkylimino)-oxy-C₁-C₈-alkyl,    (C₃-C₇-cycloalkylimino)-oxy-C₁-C₈-alkyl,    (C₁-C₆-alkylimino)-oxy-C₃-C₇-cycloalkyl,    (C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,    (C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, (benzyloxyimino)-C₁-C₈-alkyl,    C₁-C₈-alkoxyalkyl, C₁-C₈-alkylthioalkyl, C₁-C₈-alkoxyalkoxyalkyl,    C₁-C₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl,    6-membered heteroaryl, benzyloxy, phenyloxy, benzylsulfanyl,    benzylamino, phenylsulfanyl, or phenylamino;    and its salts or N-oxides.

The salts or N-oxides of the compounds of formula (I) also havefungicidal properties.

The formula (I) provides a general definition of the imidazolederivatives according to the invention. Preferred radical definitionsfor the formulae shown above and below are given below. Thesedefinitions apply to the end products of the formulae (I), (I-1),(I-2a), (I-2b), (I-1-Q-I-1), (I-1-Q-I-2), (I-1-Q-I-3), (I-1-Q-I-4) andlikewise to all intermediates.

-   R¹ preferably represents hydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl,    optionally halogen-, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl, naphthyl, thiazolyl, thienyl or a substituent of    formula Q¹, more preferably naphthyl, 1,3-thiazol-5-yl,    1,3-thiazol-4-yl, 2-thienyl, 3-thienyl or a substituent of formula    Q¹,    -   wherein    -   the naphthyl, thiazolyl, thienyl, 1,3-thiazol-5-yl,        1,3-thiazol-4-yl, 2-thienyl, 3-thienyl is non-substituted or        substituted by one or more group(s) selected from halogen,        nitro, pentafluoro-λ⁶⁻sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl        having 1 to 5 halogen atoms, C₃-C₅-cycloalkyl,        C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy,        C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, preferably is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₁-C₈-haloalkoxy        having 1 to 5 halogen atoms, more preferably is non-substituted        or substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl, methyl,        ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,        difluoromethyl, trifluoromethyl, difluoromethoxy,        trifluoromethoxy; and wherein    -   Q¹ preferably represents a 6-membered aromatic cycle of formula        (Q¹-I)

-   -   wherein U¹, U², U³, U⁴ and U⁵ are defined as outlined above and        X¹, X², X³, X⁴ and X⁵ have the preferred, more preferred or most        preferred meaning given below.

-   R¹ more preferably represents a substituent of formula Q¹, wherein    -   Q¹ represents a 6-membered aromatic cycle of formula (Q¹-I)

-   -   wherein U¹, U², U³, U⁴ and U⁵ are defined as outlined above and        X¹, X², X³, X⁴ and X⁵ have the preferred, more preferred or most        preferred meaning given below.

-   X¹, X², X³, X⁴ and X⁵ in the definitions for U¹, U², U³, U⁴ and U⁵    preferably represent independently from each other hydrogen,    halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,    C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,    C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy,    C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, aryl, aryloxy,    heteroaryl, heteroaryloxy,    -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy.

-   X¹, X², X³, X⁴ and X⁵ in the definitions for U¹, U², U³, U⁴ and U⁵    more preferably represent independently from each other hydrogen,    halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl    having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₇-halocycloalkyl    having 1 to 5 halogen atoms, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1    to 5 halogen atoms, phenyloxy, and pyridinyloxy,    -   wherein the phenyloxy, and pyridinyloxy is non-substituted or        substituted by one or more group(s) selected from halogen,        pentafluoro-λ⁶-sulfanyl, C₁-C₈-haloalkyl, and C₁-C₈-haloalkoxy,        preferably is non-substituted or substituted by one or more        group(s) selected from halogen, pentafluoro-λ⁶-sulfanyl and        C₁-C₄-haloalkyl, more preferably is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl.

-   X¹, X², X³, X⁴ and X⁵ in the definitions for U¹, U², U³, U⁴ and U⁵    more preferably represent independently from each other hydrogen,    fluorine, chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,    methyl, ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,    difluoromethyl, trifluoromethyl, cyclopropyl, fluorocyclopropyl,    chlorocyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy,    chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, phenyloxy, and    pyridinyloxy,    -   wherein the phenyloxy, and pyridinyloxy phenyloxy, and        pyridinyloxy is non-substituted or substituted by one or more        group(s) selected from halogen, pentafluoro-λ⁶-sulfanyl,        C₁-C₈-haloalkyl, and C₁-C₈-haloalkoxy, preferably is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl and C₁-C₄-haloalkyl, more        preferably is non-substituted or substituted by one or more        group(s) selected from fluorine, chlorine, bromine, iodine,        pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl.

-   X¹, X², X³, X⁴ and X⁵ in the definitions for U¹, U², U³, U⁴ and U⁵    more preferably represent independently from each other hydrogen,    fluorine, chlorine, bromine, or trifluoromethyl.

-   X¹ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, more preferably    represents hydrogen, fluorine, chlorine, bromine or trifluoromethyl,    most preferably represents hydrogen, fluorine, chlorine, or bromine.

-   X² more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen.

-   X³ more preferably represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl.

-   X³ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy.

-   X³ most preferably represents hydrogen, fluorine, chlorine, bromine    or trifluoromethyl.

-   X⁴ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen, fluorine, chlorine, bromine or trifluoromethyl.

-   X⁵ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, more preferably    represents hydrogen, fluorine, chlorine, bromine or trifluoromethyl,    most preferably represents hydrogen, fluorine, chlorine, or bromine.

-   Q¹ preferably represents a substituted 6-membered aromatic    heterocycle containing one or two nitrogen atoms or a substituted    6-membered aromatic carbocycle. Substituted means that the cycle of    the given formula comprises at least one of X¹, X², X³, X⁴ and X⁵    not being hydrogen.

-   Q¹ more preferably represents a, preferably substituted, 6-membered    aromatic cycle of formula (Q¹-I-1) to (Q¹-I-10)

wherein X¹, X², X³, X⁴ and X⁵ have the same general, preferred, morepreferred and most preferred definition as given above.

Q¹ most preferably represents a, preferably substituted, phenyl,3-pyridyl or 4-pyridyl of formula (Q¹-I-1) to (Q¹-I-3)

wherein X¹, X², X³, X⁴ or X⁵ have the same general, preferred, morepreferred and most preferred definition as given above.

In preferred embodiments of the present invention Q¹ represents a,preferably substituted, phenyl or 3-pyridyl of formula (Q¹-I-1a) or(Q¹-I-2a)

wherein X¹, X³ or X⁵ have the same general, preferred, more preferredand most preferred definition as given above.

In further preferred embodiments Q¹ represents a 3-pyridyl of formula(Q¹-I-2-1H)

wherein

-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably hydrogen;-   X³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl,    -   preferably represents hydrogen, fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or        chlorodifluoromethoxy,    -   more preferably represents hydrogen, fluorine, chlorine, bromine        or trifluoromethyl; and-   X⁵ represents fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents fluorine, chlorine,    bromine or trifluoromethyl, more preferably represents fluorine,    chlorine, or bromine.

In further preferred embodiments Q¹ represents a 3-pyridyl of formula(Q¹-I-2-5H)

wherein

-   X¹ represents fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents fluorine, chlorine,    bromine or trifluoromethyl, more preferably represents fluorine,    chlorine, or bromine;-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably hydrogen; and-   X³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl,    -   preferably represents hydrogen, fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or        chlorodifluoromethoxy, more preferably represents hydrogen,        fluorine, chlorine, bromine or trifluoromethyl.

In the most preferred embodiments of the present invention Q¹ representsa, preferably substituted, phenyl of formula (Q¹-I-1a)

wherein X¹, X³ or X⁵ have the same general, preferred, more preferredand most preferred definition as given above.

-   R^(1a) preferably represents hydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl,    optionally halogen-, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl, naphthyl, thiazolyl, preferably 1,3-thiazol-5-yl    or 1,3-thiazol-4-yl, thienyl, preferably 2-thienyl or 3-thienyl, or    a substituent of formula Q¹,    -   wherein    -   the naphthyl, thiazolyl, thienyl, 1,3-thiazol-5-yl,        1,3-thiazol-4-yl, 2-thienyl, 3-thienyl is non-substituted or        substituted by one or more group(s) selected from halogen,        nitro, pentafluoro-λ⁶⁻sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl        having 1 to 5 halogen atoms, C₃-C₅-cycloalkyl,        C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy,        C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, preferably is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₁-C₈-haloalkoxy        having 1 to 5 halogen atoms, more preferably is non-substituted        or substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl, methyl,        ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,        difluoromethyl, trifluoromethyl, difluoromethoxy,        trifluoromethoxy; and wherein    -   Q¹ preferably represents a 6-membered aromatic cycle of formula        (Q¹-I)

-   -   wherein U¹, U², U³, U⁴ and U⁵ are defined as outlined above and        X¹, X², X³, X⁴ and X⁵ have the preferred, more preferred or most        preferred meaning given below.

-   R^(1a) more preferably represents hydrogen, C₁-C₈-alkyl,    C₁-C₈-haloalkyl, optionally halogen-, C₁-C₄-alkyl-, or    C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl.

-   R^(1a) more preferably represents hydrogen, tertiary C₄-C₈-alkyl,    tertiary C₄-C₈-haloalkyl, or halogen- or C₁-C₄-alkyl-substituted    cyclopropyl.

-   R^(1a) more preferably represents hydrogen, tert-butyl, tertiary    halobutyl, fluorocyclopropyl, or chlorocyclopropyl.

-   R^(1a) most preferably represents hydrogen.

In the most preferred embodiments of the present invention R1^(a)represents hydrogen.

-   R² preferably represents C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally    halogen-, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted    C₃-C₇-cycloalkyl, naphthyl, thiazolyl, thienyl or a substituent of    formula Q², more preferably naphthyl, 1,3-thiazol-5-yl,    1,3-thiazol-4-yl, 2-thienyl, 3-thienyl or a substituent of formula    Q²,    -   wherein    -   the naphthyl, thiazolyl, thienyl, 1,3-thiazol-5-yl,        1,3-thiazol-4-yl, 2-thienyl, 3-thienyl is non-substituted or        substituted by one or more group(s) selected from halogen,        nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl        having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,        C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy,        C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, preferably is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₁-C₈-haloalkoxy        having 1 to 5 halogen atoms, more preferably is non-substituted        or substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl, methyl,        ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,        difluoromethyl, trifluoromethyl, difluoromethoxy,        trifluoromethoxy; and wherein    -   Q² preferably represents a 6-membered aromatic cycle of formula        (Q²-I)

-   -   wherein Z¹, Z², Z³, Z⁴ and Z⁵ are defined as outlined above and        Y¹, Y², Y³, Y⁴ and Y⁵ have the preferred, more preferred or most        preferred meaning given below.

-   R² more preferably represents a substituent of formula Q², wherein    -   Q² represents a 6-membered aromatic cycle of formula (Q²-I)

-   -   wherein Z¹, Z², Z³, Z⁴ and Z⁵ are defined as outlined above and        Y¹, Y², Y³, Y⁴ and Y⁵ have the preferred, more preferred or most        preferred meaning given below.

-   Y¹, Y², Y³, Y⁴ and Y⁵ in the definitions for Z¹, Z², Z³, Z⁴ and Z⁵    preferably represent independently from each other hydrogen,    halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,    C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,    C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkoxy,    C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, aryl, aryloxy,    heteroaryl, heteroaryloxy,    -   wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,        C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy.

-   Y¹, Y², Y³, Y⁴ and Y⁵ in the definitions for Z¹, Z², Z³, Z⁴ and Z⁵    more preferably represent independently from each other hydrogen,    halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl    having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₇-halocycloalkyl    having 1 to 5 halogen atoms, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1    to 5 halogen atoms, phenyloxy, and pyridinyloxy,    -   wherein the phenyloxy, and pyridinyloxy is non-substituted or        substituted by one or more group(s) selected from halogen,        pentafluoro-λ⁶-sulfanyl, C₁-C₈-haloalkyl, and C₁-C₈-haloalkoxy,        preferably is non-substituted or substituted by one or more        group(s) selected from halogen, pentafluoro-λ⁶⁻sulfanyl and        C₁-C₄-haloalkyl, more preferably is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl.

-   Y¹, Y², Y³, Y⁴ and Y⁵ in the definitions for Z¹, Z², Z³, Z⁴ and Z⁵    more preferably represent independently from each other hydrogen,    fluorine, chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,    methyl, ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,    difluoromethyl, trifluoromethyl, cyclopropyl, fluorocyclopropyl,    chlorocyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy,    chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, phenyloxy, and    pyridinyloxy,    -   wherein the phenyloxy, and pyridinyloxy phenyloxy, and        pyridinyloxy is non-substituted or substituted by one or more        group(s) selected from halogen, pentafluoro-λ⁶-sulfanyl,        C₁-C₈-haloalkyl, and C₁-C₈-haloalkoxy, preferably is        non-substituted or substituted by one or more group(s) selected        from halogen, pentafluoro-λ⁶-sulfanyl and C₁-C₄-haloalkyl, more        preferably is non-substituted or substituted by one or more        group(s) selected from fluorine, chlorine, bromine, iodine,        pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl.

-   Y¹, Y², Y³, Y⁴ and Y⁵ in the definitions for Z¹, Z², Z³, Z⁴ and Z⁵    more preferably represent independently from each other hydrogen,    fluorine, chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,    methyl, ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl,    difluoromethyl, trifluoromethyl, cyclopropyl, fluorocyclopropyl,    chlorocyclopropyl, methoxy, difluoromethoxy, trifluoromethoxy,    chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy.

-   Y¹, Y², Y³, Y⁴ and Y⁵ in the definitions for Z¹, Z², Z³, Z⁴ and Z⁵    more preferably represent independently from each other hydrogen,    fluorine, chlorine, bromine, trifluoromethyl, methoxy or    trifluoromethoxy.

-   Y¹ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen, fluorine, chlorine, or bromine.

-   Y² more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen.

-   Y³ more preferably represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl.

-   Y³ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy.

-   Y³ most preferably represents fluorine, chlorine, bromine,    trifluoromethyl, methoxy or trifluoromethoxy.

-   Y⁴ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen.

-   Y⁵ more preferably represents hydrogen, fluorine, chlorine, bromine,    methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,    trifluoromethoxy, or chlorodifluoromethoxy, most preferably    represents hydrogen, fluorine, chlorine, or bromine.

-   Q² preferably represents a substituted 6-membered aromatic    heterocycle containing one or two nitrogen atoms or a substituted    6-membered aromatic carbocycle. Substituted means that the cycle of    the given formula comprises at least one of Y¹, Y², Y³, Y⁴ and Y⁵    not being hydrogen.

-   Q² more preferably represents a, preferably substituted, phenyl,    3-pyridyl or 4-pyridyl of formula (Q²-I-1) to (Q²-I-3)

wherein Y¹, Y², Y³, Y⁴ and Y⁵ have the same general, preferred, morepreferred and most preferred definition as given above.

In preferred embodiments of the present invention Q² represents a,preferably substituted, phenyl or 3-pyridyl of formula (Q²-I-1a) or(Q²-I-2a)

wherein Y¹, Y³ or Y⁵ have the same general, preferred, more preferredand most preferred definition as given above.

In further preferred embodiments Q² represents a 3-pyridyl of formula(Q²-I-2-1H)

wherein

-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably hydrogen;-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl,    -   preferably represents hydrogen, fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or        chlorodifluoromethoxy,    -   more preferably represents fluorine, chlorine, bromine,        trifluoromethyl, methoxy or trifluoromethoxy; and-   Y⁵ represents fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents fluorine, chlorine, or    bromine.

In further preferred embodiments Q² represents a 3-pyridyl of formula(Q²-I-2-5H)

wherein

-   Y¹ represents fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents fluorine, chlorine, or    bromine;-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably hydrogen; and-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy,    -   wherein the phenyloxy and pyridin-3-yloxy is non-substituted or        substituted by one or more group(s) selected from fluorine,        chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,        difluoromethyl, trifluoromethyl,    -   preferably represents hydrogen, fluorine, chlorine, bromine,        methyl, ethyl, trifluoromethyl, methoxy, trifluoromethoxy, or        chlorodifluoromethoxy,    -   more preferably represents fluorine, chlorine, bromine,        trifluoromethyl, methoxy or trifluoromethoxy.

In the most preferred embodiments of the present invention Q² representsa, preferably substituted, phenyl of formula (Q²-I-1a)

wherein Y¹, Y³ or Y⁵ have the same general, preferred, more preferredand most preferred definition as given above.

-   R³ preferably represents halogen, hydroxyl, cyano, isocyano,    carboxaldehyde, hydroxycarbonyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl,    C₁-C₈-cyanoalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,    C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₂-C₈-alkenyl,    C₂-C₈-alkynyl, C₂-C₈-alkenyloxy, C₂-C₈-haloalkenyloxy,    C₃-C₈-alkynyloxy, C₃-C₈-haloalkynyloxy, C₁-C₈-alkylsulfanyl,    C₁-C₈-haloalkylsulfanyl, C₁-C₈-alkylcarbonyl,    C₁-C₈-haloalkylcarbonyl, arylcarbonyl, aryl-C₁-C₆-alkylcarbonyl,    C₃-C₈-cycloalkylcarbonyl, C₃-C₈-halocycloalkylcarbonyl,    aminothiocarbonyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-haloalkoxycarbonyl,    C₃-C₈-cycloalkoxycarbonyl, C₁-C₈-alkylcarbonyloxy,    C₁-C₈-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy, benzyl,    phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, or    phenyloxy, wherein the benzyl, phenyl, 5-membered heteroaryl,    6-membered heteroaryl, benzyloxy or phenyloxy may be optionally    substituted by one or more group(s) selected from halogen, hydroxyl,    cyano, isocyano, amino, sulfanyl, pentafluoro-λ⁶-sulfanyl,    C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,    tri(C₁-C₈-alkyl)silyl, C₃-C₇-cycloalkyl, C₂-C₈-alkenyl,    C₂-C₈-alkynyl.-   R³ more preferably represents halogen, cyano, carboxaldehyde,    hydroxycarbonyl, C₂-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-cyanoalkyl,    C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy, C₃-C₇-cycloalkyl,    C₃-C₇-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,    C₁-C₈-alkylsulfanyl, C₁-C₈-haloalkylsulfanyl, C₁-C₈-alkylcarbonyl,    C₁-C₈-haloalkylcarbonyl, aminothiocarbonyl, C₁-C₈-alkoxycarbonyl,    C₁-C₈-haloalkoxycarbonyl, benzyl, phenyl, 5-membered heteroaryl,    6-membered heteroaryl, benzyloxy, or phenyloxy, wherein the benzyl,    phenyl, 5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or    phenyloxy may be optionally substituted by one or more group(s)    selected from halogen, hydroxyl, cyano, amino, sulfanyl,    pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl,    C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy, tri(C₁-C₈-alkyl)silyl,    C₃-C₇-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl.-   R³ more preferably represents halogen, cyano, carboxaldehyde,    hydroxycarbonyl, C₂-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl,    C₁-C₄-alkyloxy, C₁-C₄-haloalkyloxy, C₃-C₇-cycloalkyl,    C₃-C₇-halocycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,    C₁-C₄-alkylsulfanyl, C₁-C₄-haloalkylsulfanyl, C₁-C₄-alkylcarbonyl,    C₁-C₄-haloalkylcarbonyl, aminothiocarbonyl, C₁-C₄-alkoxycarbonyl,    C₁-C₄-haloalkoxycarbonyl, benzyl, phenyl, fulyl, pyrrolyl, thienyl,    pyridyl, benzyloxy, or phenyloxy, wherein the benzyl, phenyl,    5-membered heteroaryl, 6-membered heteroaryl, benzyloxy or phenyloxy    may be optionally substituted by one or more group(s) selected from    halogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy,    C₁-C₈-haloalkyloxy.-   R³ more preferably represents fluorine, chlorine, bromine, iodine,    cyano, hydroxycarbonyl, carboxaldehyde, C₂-C₄-alkyl,    C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₁-C₄-alkyloxy, C₃-C₇-cycloalkyl,    C₂-C₈-alkynyl, C₁-C₄-alkylsulfanyl, C₁-C₄-alkylcarbonyl,    aminothiocarbonyl, C₁-C₄-alkoxycarbonyl, phenyl, or thienyl, wherein    the phenyl or thienyl may be optionally substituted by one or more    group(s) selected from halogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl,    C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy.-   R³ more preferably represents fluorine, chlorine, bromine, iodine,    cyano, hydroxycarbonyl, carboxaldehyde, trifluoromethyl,    cyanomethyl, methoxy, methylsulfanyl, cyclopropyl, ethinyl,    methylcarbonyl (acetyl), carboxyl, aminothiocarbonyl,    methoxycarbonyl, ethoxycarbonyl, phenyl, or 2-thienyl.-   R³ more preferably represents fluorine; chlorine; bromine; iodine;    or cyano.-   R³ more preferably represents chlorine, fluorine or cyano.-   R³ most preferably represents cyano.

In preferred embodiments of the invention R¹ represents a substituent offormula Q¹, wherein Q¹ is defined in general, preferred, more preferredand most preferred terms as outlined above, R^(1a) represents hydrogen,R² represents a substituent of formula Q², wherein Q² is defined ingeneral, preferred, more preferred and most preferred terms as outlinedabove, and R³ is defined in general, preferred, more preferred and mostpreferred terms as outlined above.

In such preferred embodiments R³ preferably represents fluorine;chlorine; bromine; iodine or cyano, more preferably cyano.

A preferred embodiment of the present invention relates to compounds offormula (I-1)

wherein R³, U³, U⁴, X¹, X², X⁵, Z³, Z⁴, Y¹, Y² and Y⁵ have the samegeneral, preferred, more preferred and most preferred definition asgiven for formula (I).

A more preferred embodiment of the present invention relates tocompounds of formula (I-1-Q-I-1)

wherein R³, X¹, X², X³, X⁴, X⁵, Y¹, Y², Y³, Y⁴ and Y⁵ have the samegeneral, preferred, more preferred and most preferred definition asgiven for formula (I).

Particularly preferred are compounds of formula (I-1-Q-I-1)

wherein

-   R³ represents fluorine, chlorine, bromine, iodine, cyano,    hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl,    methoxy, methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl    (acetyl), carboxyl, aminothiocarbonyl, methoxycarbonyl,    ethoxycarbonyl, phenyl, or 2-thienyl, preferably fluorine, chlorine,    bromine, cyano, or trifluoromethyl, more preferably fluorine,    chlorine, or cyano;-   X¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   X³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents hydrogen,    fluorine, chlorine, bromine or trifluoromethyl;-   X⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   Y¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine;-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents fluorine,    chlorine, bromine, trifluoromethyl, methoxy, or trifluoromethoxy;-   Y⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen; and-   Y⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine.

Even more preferred are compounds of formula (I-1-Q-I-1)

wherein

-   R³ represents fluorine, chlorine, or cyano;-   X¹ represents hydrogen;-   X² represents hydrogen;-   X³ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   X⁴ represents hydrogen;-   X⁵ represents fluorine, chlorine, or bromine;-   Y¹ represents hydrogen;-   Y² represents hydrogen;-   Y³ represents fluorine, chlorine, bromine, trifluoromethyl, methoxy,    or trifluoromethoxy;-   Y⁴ represents hydrogen; and-   Y⁵ represents hydrogen, fluorine, chlorine, or bromine.

Further particularly preferred are compounds of formula (I-1-Q-I-2)

wherein

-   R³ represents fluorine, chlorine, bromine, iodine, cyano,    hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl,    methoxy, methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl    (acetyl), carboxyl, aminothiocarbonyl, methoxycarbonyl,    ethoxycarbonyl, phenyl, or 2-thienyl, preferably fluorine, chlorine,    bromine, cyano, or trifluoromethyl, more preferably fluorine,    chlorine, or cyano;-   X¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   X³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents hydrogen,    fluorine, chlorine, bromine or trifluoromethyl;-   X⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   Y¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine;-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents fluorine,    chlorine, bromine, trifluoromethyl, methoxy, or trifluoromethoxy;-   Y⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen; and-   Y⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine.

Further particularly preferred are compounds of formula (I-1-Q-I-3)

wherein

-   R³ represents fluorine, chlorine, bromine, iodine, cyano,    hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl,    methoxy, methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl    (acetyl), carboxyl, aminothiocarbonyl, methoxycarbonyl,    ethoxycarbonyl, phenyl, or 2-thienyl, preferably fluorine, chlorine,    bromine, cyano, or trifluoromethyl, more preferably fluorine,    chlorine, or cyano;-   X¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   X⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   Y¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine;-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents fluorine,    chlorine, bromine, trifluoromethyl, methoxy, or trifluoromethoxy;-   Y⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen; and-   Y⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine.

Particularly preferred are also compounds of formula (I-1-Q-I-4)

wherein

-   R³ represents fluorine, chlorine, bromine, iodine, cyano,    hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl,    methoxy, methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl    (acetyl), carboxyl, aminothiocarbonyl, methoxycarbonyl,    ethoxycarbonyl, phenyl, or 2-thienyl, preferably fluorine, chlorine,    bromine, cyano, or trifluoromethyl, more preferably fluorine,    chlorine, or cyano;-   X¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   X³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents hydrogen,    fluorine, chlorine, bromine or trifluoromethyl;-   X⁴ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   X⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, bromine or trifluoromethyl;-   Y¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine;-   Y² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen;-   Y³ represents hydrogen, fluorine, chlorine, bromine,    pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-,    iso-, sec-, tert-butyl, difluoromethyl, trifluoromethyl,    cyclopropyl, fluorocyclopropyl, chlorocyclopropyl, methoxy,    trifluoromethoxy, chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy,    phenyloxy and pyridin-3-yloxy, wherein the phenyloxy and    pyridin-3-yloxy is non-substituted or substituted by one or more    group(s) selected from fluorine, chlorine, bromine, iodine,    pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, preferably    represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, more preferably represents fluorine,    chlorine, bromine, trifluoromethyl, methoxy, or trifluoromethoxy;    and-   Y⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,    difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, or    chlorodifluoromethoxy, preferably represents hydrogen, fluorine,    chlorine, or bromine.

Particularly preferred are also compounds of formula (I-2a) and (I-2b)

-   wherein R¹ represents a substituent of formula Q¹, wherein Q¹ has    the same general, preferred, more preferred and most preferred    definition as given for formula (I);-   R² represents a substituent of formula Q², wherein Q² has the same    general, preferred, more preferred and most preferred definition as    given for formula (I); and-   R³ has the same general, preferred, more preferred and most    preferred definition as given for formula (I).

In such compounds R¹ and R² are located in trans-position versus eachother.

The radical definitions and explanations given above in general terms orstated within preferred ranges can be combined with one another asdesired, i.e. including between the particular ranges and preferredranges. They apply both to the end products and correspondingly toprecursors and intermediates. In addition, individual definitions maynot apply.

Preference is given to those compounds of the formula (I) in which eachof the radicals have the abovementioned preferred definitions.

Particular preference is given to those compounds of the formula (I) inwhich each of the radicals have the abovementioned more preferreddefinitions.

Very particular preference is given to those compounds of the formula(I) in which each of the radicals have the above mentioned mostpreferred definitions.

In the definitions of the symbols given in the above formulae,collective terms were used which are generally representative of thefollowing substituents:

The definition C₁-C₈-alkyl comprises the largest range defined here foran alkyl radical. Specifically, this definition comprises the meaningsmethyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl, and also ineach case all isomeric pentyls, hexyls, heptyls and octyls, such asmethyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl,2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl,2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl,2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl,2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethylbutyl, 2-ethylbutyl,1-ethyl-3-methylpropyl, n-heptyl, 1-methylhexyl, 1-ethylpentyl,2-ethylpentyl, 1-propylbutyl, octyl, 1-methylheptyl, 2-methylheptyl,1-ethylhexyl, 2-ethylhexyl, 1-propylpentyl and 2-propylpentyl, inparticular propyl, 1-methylethyl, butyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 1,1-dimethylethyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,pentyl, 1-methylbutyl, 1-ethylpropyl, hexyl, 3-methylpentyl, heptyl,1-methylhexyl, 1-ethyl-3-methylbutyl, 1-methylheptyl, 1,2-dimethylhexyl,1,3-dimethyloctyl, 4-methyloctyl, 1,2,2,3-tetramethylbutyl,1,3,3-trimethylbutyl, 1,2,3-trimethylbutyl, 1,3-dimethylpentyl,1,3-dimethylhexyl, 5-methyl-3-hexyl, 2-methyl-4-heptyl and1-methyl-2-cyclopropylethyl. A preferred range is C₁-C₄-alkyl, such asmethyl, ethyl, n-, isopropyl, n-, iso-, sec-, tert-butyl. The definitionC₁-C₃-alkyl comprises methyl, ethyl, n-, isopropyl.

The definition halogen comprises fluorine, chlorine, bromine and iodine.Halogen-substitution is generally indicated by the prefix halo, halogenor halogeno.

Halogen-substituted alkyl—referred to as haloalkyl, halogenalkyl orhalogenoalkyl—represents, for example, C₁-C₈-alkyl as defined abovesubstituted by one or more halogen substituents which can be the same ordifferent. Preferably C₁-C₈-haloalkyl represents chloromethyl,dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl,2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl,2,2,2-trichloroethyl, pentafluoroethyl, 1-fluoro-1-methylethyl,2-fluoro-1,1-dimethylethyl, 2-fluoro-1-fluoromethyl-1-methylethyl,2-fluoro-1,1-di(fluoromethyl)-ethyl, 3-chloro-1-methylbutyl,2-chloro-1-methylbutyl, 1-chlorobutyl, 3,3-dichloro-1-methylbutyl,3-chloro-1-methylbutyl, 1-methyl-3-trifluoromethylbutyl,3-methyl-1-trifluoromethylbutyl.

Mono- or multiple fluorinated C₁-C₄-alkyl represents, for example,C₁-C₄-alkyl as defined above substituted by one or more fluorinesubstituent(s). Preferably mono- or multiple fluorinated C₁-C₄-alkylrepresents fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl,2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,pentafluoroethyl, 1-fluoro-1-methylethyl, 2-fluoro-1,1-dimethylethyl,2-fluoro-1-fluoromethyl-1-methylethyl,2-fluoro-1,1-di(fluoromethyl)-ethyl, 1-methyl-3-trifluoromethylbutyl,3-methyl-1-trifluoromethylbutyl.

The definition C₂-C₈-alkenyl comprises the largest range defined herefor an alkenyl radical. Specifically, this definition comprises themeanings ethenyl, n-, isopropenyl, n-, iso-, sec-, tert-butenyl, andalso in each case all isomeric pentenyls, hexenyls, heptenyls, octenyls,1-methyl-1-propenyl, 1-ethyl-1-butenyl, 2,4-dimethyl-1-pentenyl,2,4-dimethyl-2-pentenyl. Halogen-substituted alkenyl—referred to ashaloalkenyl, halogenalkenyl or halogenoalkenyl—represents, for example,C₂-C₈-alkenyl as defined above substituted by one or more halogensubstituents which can be the same or different. A preferred range isC₂-C₄-alkenyl, such as ethenyl, n-, isopropenyl, n-, iso-, sec- ortert-butenyl.

The definition C₂-C₈-alkynyl comprises the largest range defined herefor an alkynyl radical. Specifically, this definition comprises themeanings ethynyl, n-, isopropynyl, n-, iso-, sec-, tert-butynyl, andalso in each case all isomeric pentynyls, hexynyls, heptynyls, octynyls.Halogen-substituted alkynyl—referred to as haloalkynyl, halogenalkynylor halogenoalkynyl—represents, for example, C₂-C₅-alkynyl as definedabove substituted by one or more halogen substituents which can be thesame or different. A preferred range is C₂-C₄-alkynyl, such as ethynyl,n-, isopropynyl, n-, iso-, sec- or tert-butynyl.

The definition C₃-C₇-cycloalkyl comprises monocyclic saturatedhydrocarbyl groups having 3 to 7 carbon ring members, such ascyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.

The definition halogen-substituted cycloalkyl and halocycloalkylcomprises monocyclic saturated hydrocarbyl groups having 3 to 7 carbonring members, such as 1-fluoro-cyclopropyl and 1-chlorocyclopropyl.

The definition bicycloalkyl comprises spirocyclic alkyl wherein twosubstituents at the same carbon atom of a C₃-C₇-cycloalkyl can formtogether with the carbon atom to which they are attached aC₃-C₇-cycloalkyl, this definition comprises for example the meaningspiro[2.2]pentyl. The definition bicycloalkyl also comprises bicyclicalkyls wherein two substituents at different adjacent or non-adjacentcarbon atoms of a C₃-C₇-cycloalkyl can form together with the carbonatoms to which they are attached a C₃-C₇-cycloalkyl, this definitioncomprises for example the meaning bicyclo[2.2.1]heptane-2-yl,bicyclo[2.2.1]heptane-7-yl, bicyclo[4.1.0]heptane-2-yl,bicyclo[4.1.0]heptane-3-yl, bicyclo[4.1.0]heptane-7-yl The definitionbicycloalkyl also comprises bicyclic alkyls wherein two substituents atdifferent adjacent or non-adjacent carbon atoms of a C₃-C₇-cycloalkylcan form an alkylene bridge between the carbon atoms to which they areattached, this definition comprises for example the meaningbicyclo[2.2.1]hept-2-ene-2-yl, bicyclo[2.2.1]hept-2-ene-5-yl,bicyclo[2.2.1]hept-2-ene-7-yl.

The definition aryl comprises aromatic, mono-, bi- or tricycliccarbocycles, for example phenyl, naphthyl, anthracenyl (anthyl),phenanthracenyl (phenanthyl).

The definition hetaryl or heteroaryl comprises unsaturated,benzoannulated or not benzoannulated heterocyclic 5- to 10-membered ringcontaining up to 4 heteroatoms selected from N, O and S. Preferably Thedefinition hetaryl or heteroaryl comprises unsubstituted or substituted,unsaturated heterocyclic 5- to 7-membered ring containing up to 4heteroatoms selected from N, O and S: for example 2-furyl, 3-furyl,2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl,4-pyrazolyl, 5-pyrazolyl, 1-pyrazolyl, 1H-imidazol-2-yl,1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-imidazol-1-yl, 2-oxazolyl,4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 1H-1,2,3-triazol-1-yl,1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl, 2H-1,2,3-triazol-2-yl,2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl,1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-3-yl, 4H-1,2,4-triazol-4-yl,1H-tetrazol-1-yl, 1H-tetrazol-5-yl, 2H-tetrazol-2-yl, 2H-tetrazol-5-yl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl,1,2,3-oxadiazol-4-yl, 1,2,3-oxadiazol-5-yl, 1,2,3-thiadiazol-4-yl,1,2,3-thiadiazol-5-yl, 1,2,5-oxadiazol-3-yl, 1,2,5-thiadiazol-3-yl,2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl,2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl,1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl,1,2,4-triazin-6-yl.

The definition 5-membered heteroaryl comprises an unsaturatedheterocyclic 5-membered ring containing up to 4 heteroatoms selectedfrom N, O and S: for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl,2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 1-pyrazolyl, 1H-imidazol-2-yl, 1H-imidazol-4-yl,1H-imidazol-5-yl, 1H-imidazol-1-yl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl,2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl,5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl,1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl, 1H-1,2,3-triazol-5-yl,2H-1,2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1,2,4-triazol-3-yl,1H-1,2,4-triazol-5-yl, 1H-1,2,4-triazol-1-yl, 4H-1,2,4-triazol-3-yl,4H-1,2,4-triazol-4-yl, 1H-tetrazol-1-yl, 1H-tetrazol-5-yl,2H-tetrazol-2-yl, 2H-tetrazol-5-yl, 1,2,4-oxadiazol-3-yl,1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl,1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-oxadiazol-4-yl,1,2,3-oxadiazol-5-yl, 1,2,3-thiadiazol-4-yl, 1,2,3-thiadiazol-5-yl,1,2,5-oxadiazol-3-yl, 1,2,5-thiadiazol-3-yl.

The definition 6-membered heteroaryl comprises an unsaturatedheterocyclic 6-membered ring containing up to 4 heteroatoms selectedfrom N, O and S: for example 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl,1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl.

The definition heterocycloalkyl comprises saturated or partiallyunsaturated mono-, bi- or tricyclic ring systems consisting of C-atomsand containing up to 4 heteroatoms selected from N, O and S: for exampleaziridinyl, pyrrolidinyl, dihydropyridyl, piperidinyl, piperazinyl,morpholinyl, thiomorpholinyl, tetrahydrofuranyl, tetrahydrothiofuranyl,tetrahydropyranyl, pyranyl, isoxazolidinyl, isoxazolinyl, pyrazolinyl,dihydropyrrolyl, tetrahydropyridinyl, dioxolanyl, dioxanyl,oxathiolanyl, oxathianyl, dithiolanyl, dithianyl. The term partiallyunsaturated refers to ring systems that are neither saturated, i.e.comprising no double bound, nor fully unsaturated, i.e. comprising themaximum possible number of double bonds. In other words, partiallyunsaturated ring systems comprise at least one double bond, but not themaximum possible number of double bonds.

Optionally substituted radicals may be mono- or polysubstituted, wherein the case of polysubstitution, the substituents may be identical ordifferent.

Unless indicated otherwise, a group or a substituent which issubstituted according to the invention preferably can be substituted byone or more group(s) selected from the list consisting of halogen, SH,nitro, hydroxyl, cyano, amino, sulfanyl, pentafluoro-λ⁶-sulfanyl,formyl, formyloxy, formylamino, carbamoyl, N-hydroxycarbamoyl,carbamate, (hydroxyimino)-C₁-C₆-alkyl, C₁—C-alkyl, C₁-C₈-halogenalkyl,C₁-C₈-alkyloxy, C₁-C₈-halogenalkyloxy, C₁-C₈-alkylthio,C₁-C₈-halogenalkylthio, tri(C₁-C₈-alkyl)silyl,tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-halocycloalkyl, C₃-C₇-cycloalkenyl, C₃-C₈-halocycloalkenyl,C₄-C₁₀-cycloalkylalkyl, C₄-C₁₀-halocycloalkylalkyl,C₆-C₁₂-cycloalkylcycloalkyl, tri(C₁—C₈-alkyl)silyl-C₃-C₇-cycloalkyl,C₁-C₈-halogenoalkyl, C₃-C₇-halogenocycloalkyl, C₂-C₈-alkenyl,C₂-C₈-alkynyl, C₂-C₈-alkenyloxy, C₂-C₈-halogenalkenyloxy,C₂-C₈-alkynyloxy, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino,C₁-C₈-halogenalkylamino, di-C₁-C₈-halogenalkylamino,C₁-C₈-alkylaminoalkyl, di-C₁-C₈-alkylaminoalkyl, C₁-C₈-alkoxy,C₁-C₈-halogenoalkoxy, C₁-C₈-cyanoalkoxy, C₄-C₈-cycloalkylalkoxy,C₃-C₆-cycloalkoxy, C₂-C₈-alkoxyalkoxy, C₁-C₈-alkylcarbonylalkoxy,C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl, C₂-C₈-alkenyloxy,C₂-C₈-halogenoalkenyloxy, C₃-C₈-alkynyloxy, C₃-C₈-halogenoalkynyloxy,C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl,C₃-C₈-cycloalkylcarbonyl, C₃-C₈-halogenocycloalkylcarbonyl,C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl,N—C₁-C₈-alkyloxycarbamoyl, C₁-C₈-alkoxycarbamoyl,N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, C₁-C₈-alkoxycarbonyl,C₁-C₈-halogenoalkoxycarbonyl, C₃-C₈-cycloalkoxycarbonyl,C₂-C₈-alkoxyalkylcarbonyl, C₂-C₈-halogenoalkoxyalkylcarbonyl,C₃-C₈-cycloalkoxyalkylcarbonyl, C₁-C₈-alkylaminocarbonyl,di-C₁-C₈-alkylaminocarbonyl, C₃-C₈-cycloalkylaminocarbonyl,C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy,C₃-C₈-cycloalkylcarbonyloxy, C₁-C₈-alkylcarbonylamino,C₁-C₈-halogenoalkylcarbonylamino, C₁-C₈-alkylaminocarbonyloxy,di-C₁-C₈-alkylaminocarbonyloxy, C₁-C₈-alkyloxycarbonyloxy,C₁-C₈-alkylsulfinyl, C₁-C₈-halogenoalkylsulfinyl, C₁-C₈-alkylsulfonyl,C₁-C₈-halogenoalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-halogenoalkylsulfonyloxy, C₁-C₈-alkylaminosulfamoyl,di-C₁-C₈-alkylaminosulfamoyl, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,(C₃-C₇-cycloalkoxyimino)-C₁-C₈-alkyl, hydroxyimino-C₁-C₈-alkyl,(C₁-C₈-alkoxyimino)-C₃-C₇-cycloalkyl, hydroxyimino-C₃-C₇-cycloalkyl,(C₁-C₈-alkylimino)-oxy, (C₁-C₈-alkylimino)-oxy-C₁-C₈-alkyl,(C₃-C₇-cycloalkylimino)-oxy-C₁-C₈-alkyl,(C₁-C₆-alkylimino)-oxy-C₃-C₇-cycloalkyl,(C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,(C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, 2-oxopyrrolidin-1-yl,(benzyloxyimino)-C₁-C₈-alkyl, C₁-C₈-alkoxyalkyl, C₁-C₈-alkylthioalkyl,C₁-C₈-alkoxyalkoxyalkyl, C₁-C₈-halogenoalkoxyalkyl, benzyl, phenyl,5-membered heteroaryl, 6-membered heteroaryl, benzyloxy, phenyloxy,benzylsulfanyl, benzylamino, phenoxy, phenylsulfanyl, or phenylamino,wherein the benzyl, phenyl, 5-membered heteroaryl, 6-memberedheteroaryl, benzyloxy or phenyloxy may be optionally substituted by oneor more group(s) selected from the aforementioned list.

Depending on the nature of the substituents, the compounds according tothe invention can be present as mixtures of different possible isomericforms, in particular of stereoisomers, such as, for example, E and Z,threo and erythro, and also optical isomers, and, if appropriate, alsoof tautomers. What is claimed are both the E and the Z isomers, and alsothe threo and erythro, and the optical isomers, any mixtures of theseisomers, and the possible tautomeric forms.

Depending on the nature of the substituents, the compounds of thepresent invention can exist in one or more optical or chiral isomerforms depending on the number of asymmetric centres in the compound. Theinvention thus relates equally to all the optical isomers and to theirracemic or scalemic mixtures (the term “scalemic” denotes a mixture ofenantiomers in different proportions) and to the mixtures of all thepossible stereoisomers, in all proportions. The diastereoisomers and/orthe optical isomers can be separated according to the methods which areknown per se by the man ordinary skilled in the art.

Depending on the nature of the substituents, the compounds of thepresent invention can also exist in one or more geometric isomer formsdepending on the number of double bonds in the compound. The inventionthus relates equally to all geometric isomers and to all possiblemixtures, in all proportions. The geometric isomers can be separatedaccording to general methods, which are known per se by the man ordinaryskilled in the art.

Depending on the nature of the substituents, the compounds of thepresent invention can also exist in one or more geometric isomer formsdepending on the relative position (syn/anti or cis/trans) of thesubstituents of a ring. The invention thus relates equally to allsyn/anti (or cis/trans) isomers and to all possible syn/anti (orcis/trans) mixtures, in all proportions. The syn/anti (or cis/trans)isomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Illustration of the Processes and Intermediates

The present invention furthermore relates to processes for preparingcompounds of formula (I).

The compounds of formula (I), also referred to compounds (I) can beobtained by the synthetic routes shown schematically below and in theexperimental part of this application. Unless indicated otherwise, theradicals R¹, R^(1a), R² and R³ have the meanings given above for thecompounds of formula (I). These definitions apply not only to the endproducts of formula (I) but likewise to all intermediates.

Process A (Scheme 1):

The imidazoles of formula (II) which are commercially available or canbe obtained by means of methods described in the literature, can beconverted into imidazoles of formula (II) by means of methods describedin the literature (see e.g “Protective groups in organic synthesis”,Wiley Interscience, 1999; 3^(rd) edition, T. Greene & P. Wuts, p.615-632 and references cited therein, Journal of organic chemistry(2013), 78, 12220-12223). The reaction is optionally done in thepresence of a base, such as potassium carbonate, triethylamine, and/orpotassium tert-butoxide, optionally in the presence of a Lewis acid,such as magnesium dichloride or BF₃/Et₂0, optionally in the presence ofa metal oxide, such as zinc oxide or barium oxide.

Process B (Scheme 2):

Alcohols of formula (IV), which can be obtained by means of methodsdescribed in the literature (e.g. U.S. Pat. No. 4,940,717, US-A2005/159607), can be converted into compounds of formula (V) by means ofmethods described in the literature (e.g. WO-A 2005/56548, US-A2011/295019). The reaction is optionally done in the presence of a base,such as N,N-dimethyl-cyclohexylamine or triethylamine.

The imidazoles of formula (II) can consequently react with compounds offormula (V) to give imidazolium salts of formula (VI) by means ofmethods described in the literature (see e.g “Protective groups inorganic synthesis”, Wiley Interscience, 1999; 3^(rd) edition, T. Greene& P. Wuts, p. 615-632 and references cited therein, Journal of organicchemistry (2013), 78, 12220-12223). The reaction is optionally run inthe presence of a base, such as potassium carbonate, triethylamine,and/or potassium tert-butoxide, optionally in the presence of a Lewisacid, such as magnesium dichloride or BF₃/Et₂0, optionally in thepresence of a metal oxide, such as zinc oxide or barium oxide. Allcommon solvents inert under the reaction conditions, such as for examplenitriles (such as e.g. acetonitrile, propionitrile) or alcohols (such ase.g. methanol, ethanol), can be used and the reaction can be effected inmixtures of two or more of these solvents.

Finally, imidazolium salts of formula (VI) can be converted intocompounds of formula (I) by means of methods described in the literature(see e.g “Protective groups in organic synthesis”, Wiley Interscience,1999; 3^(rd) edition, T. Greene & P. Wuts, p. 615-632 and referencescited therein, Journal of organic chemistry (2013), 78, 12220-12223).All common solvents inert under the reaction conditions, such as forexample nitriles (such as e.g. acetonitrile, propionitrile) orhalogenated solvent (such as e.g. dichloromethane or chloroform) can beused and the reaction can be effected in mixtures of two or more ofthese solvents.

The preferred compounds of the formulae (I-1), (I-2a), (I-2b),(I-1-Q-I-1), (I-1-Q-I-2), (I-1-Q-I-3) and (I-1-Q-I-4) can also beobtained according to the processes A to B according to the invention.

General

The processes A to B according to the invention for preparing compoundsof the formula (I) are optionally performed using one or more reactionauxiliaries.

Useful reaction auxiliaries are, as appropriate, inorganic or organicbases or acid acceptors. These preferably include alkali metal oralkaline earth metal acetates, amides, carbonates, hydrogencarbonates,hydrides, hydroxides or alkoxides, for example sodium acetate, potassiumacetate or calcium acetate, lithium amide, sodium amide, potassium amideor calcium amide, sodium carbonate, potassium carbonate or calciumcarbonate, sodium hydrogencarbonate, potassium hydrogencarbonate orcalcium hydrogencarbonate, lithium hydride, sodium hydride, potassiumhydride or calcium hydride, lithium hydroxide, sodium hydroxide,potassium hydroxide or calcium hydroxide, n-butyllithium,sec-butyllithium, tert-butyllithium, lithium diisopropylamide, lithiumbis(trimethylsilyl)amide, sodium methoxide, ethoxide, n- or i-propoxide,n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- ori-propoxide, n-, i-, s- or t-butoxide; and also basic organic nitrogencompounds, for example trimethylamine, triethylamine, tripropylamine,tributylamine, ethyldiisopropylamine, N,N-dimethylcyclohexylamine,dicyclohexylamine, ethyldicyclohexylamine, N,N-dimethylaniline,N,N-dimethylbenzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-,2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine,5-ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine,1,4-diazabicyclo[2.2.2]-octane (DABCO),1,5-diazabicyclo[4.3.0]-non-5-ene (DBN) or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

Further useful reaction auxiliaries are, as appropriate, inorganic ororganic acids. These preferably include inorganic acids, for examplehydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogeniodide, sulphuric acid, phosphoric acid and nitric acid, and acidicsalts such as NaHSO₄ and KHSO₄, or organic acids, for example, formicacid, carbonic acid and alkanoic acids such as acetic acid,trifluoroacetic acid, trichloroacetic acid and propionic acid, and alsoglycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid,benzoic acid, cinnamic acid, oxalic acid, saturated or mono- ordiunsaturated C₆-C₂₀ fatty acids, alkylsulphuric monoesters,alkylsulphonic acids (sulphonic acids having straight-chain or branchedalkyl radicals having 1 to 20 carbon atoms), aiylsulphonic acids oraiyldisulphonic acids (aromatic radicals, such as phenyl and naphthyl,which bear one or two sulphonic acid groups), alkylphosphonic acids(phosphonic acids having straight-chain or branched alkyl radicalshaving 1 to 20 carbon atoms), alylphosphonic acids or aryldiphosphonicacids (aromatic radicals, such as phenyl and naphthyl, which bear one ortwo phosphonic acid radicals), where the alkyl and aryl radicals maybear further substituents, for example p-toluenesulphonic acid,salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid,2-acetoxybenzoic acid, etc.

The processes A to B according to the invention are optionally performedusing one or more diluents. Useful diluents are virtually all inertorganic solvents. Unless otherwise indicated for the above describedprocesses A to B, these preferably include aliphatic and aromatic,optionally halogenated hydrocarbons, such as pentane, hexane, heptane,cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene,xylene, methylene chloride, ethylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, ethers such asdiethyl ether, dibutyl ether and methyl tert-butyl ether, glycoldimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane,ketones such as acetone, methyl ethyl ketone, methyl isopropyl ketoneand methyl isobutyl ketone, esters, such as methyl acetate and ethylacetate, nitriles, for example acetonitrile and propionitrile, amides,for example dimethylformamide, dimethylacetamide andN-methylpyrrolidone, and also dimethyl sulphoxide,tetramethylenesulphone and hexamethylphosphoramide and DMPU.

In the processes according to the invention, the reaction temperaturescan be varied within a relatively wide range. In general, thetemperatures employed are between −78° C. and 250° C., preferablytemperatures between −78° C. and 150° C.

The reaction time varies as a function of the scale of the reaction andof the reaction temperature, but is generally between a few minutes and48 hours.

The processes according to the invention are generally performed understandard pressure. However, it is also possible to work under elevatedor reduced pressure.

For performance of the processes according to the invention, thestarting materials required in each case are generally used inapproximately equimolar amounts. However, it is also possible to use oneof the components used in each case in a relatively large excess.

After a reaction has ended, the compounds are optionally separated fromthe reaction mixture by one of the customary separation techniques. Ifnecessary, the compounds are purified by recrystallization orchromatography.

If appropriate, in the processes A to B according to the invention alsosalts and/or N-oxides of the starting compounds can be used.

The compounds of the formula (I) according to the invention can beconverted into physiologically acceptable salts, e.g. as acid additionsalts or metal salt complexes.

Depending on the nature of the substituents defined above, the compoundsof the formula (I) have acidic or basic properties and can form salts,if appropriate also inner salts, or adducts with inorganic or organicacids or with bases or with metal ions. If the compounds of the formula(I) carry amino, alkylamino or other groups which induce basicproperties, these compounds can be reacted with acids to give salts, orthey are directly obtained as salts in the synthesis. If the compoundsof the formula (I) carries hydroxyl, carboxyl or other groups whichinduce acidic properties, these compounds can be reacted with bases togive salts. Suitable bases are, for example, hydroxides, carbonates,bicarbonates of the alkali metals and alkaline earth metals, inparticular those of sodium, potassium, magnesium and calcium,furthermore ammonia, primary, secondary and tertialy amines having(C₁-C₄)-alkyl groups, mono-, di- and trialkanolamines of(C₁-C₄)-alkanols, choline and also chlorocholine.

The salts obtainable in this manner also have fungicidal properties.

Examples of inorganic acids are hydrohalic acids, such as hydrogenfluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide,sulphuric acid, phosphoric acid and nitric acid, and acidic salts, suchas NaHSO₄ and KHSO₄. Suitable organic acids are, for example, formicacid, carbonic acid and alkanoic acids, such as acetic acid,trifluoroacetic acid, trichloroacetic acid and propionic acid, and alsoglycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid,benzoic acid, cinnamic acid, maleic acid, fumaric acid, tartaric acid,sorbic acid oxalic acid, alkylsulphonic acids (sulphonic acids havingstraight-chain or branched alkyl radicals of 1 to 20 carbon atoms),arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such asphenyl and naphthyl, which carry one or two sulphonic acid groups),alkylphosphonic acids (phosphonic acids having straight-chain orbranched alkyl radicals of 1 to 20 carbon atoms), arylphosphonic acidsor aryldiphosphonic acids (aromatic radicals, such as phenyl andnaphthyl, which cary one or two phosphonic acid radicals), where thealkyl and aryl radicals may carry further substituents, for examplep-toluenesulphonic acid, 1,5-naphthalenedisulphonic acid, salicylicacid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoicacid, etc.

Suitable metal ions are in particular the ions of the elements of thesecond main group, in particular calcium and magnesium, of the third andfourth main group, in particular aluminium, tin and lead, and also ofthe first to eighth transition group, in particular chromium, manganese,iron, cobalt, nickel, copper, zinc and others. Particular preference isgiven to the metal ions of the elements of the fourth period. Here, themetals can be present in various valencies that they can assume.

The acid addition salts of the compounds of the formula (I) can beobtained in a simple manner by customary methods for forming salts, forexample by dissolving a compound of the formula (I) in a suitable inertsolvent and adding the acid, for example hydrochloric acid, and beisolated in a known manner, for example by filtration, and, if required,be purified by washing with an inert organic solvent.

Suitable anions of the salts are those which are preferably derived fromthe following acids: hydrohalic acids, such as, for example,hydrochloric acid and hydrobromic acid, furthermore phosphoric acid,nitric acid and sulphuric acid.

The metal salt complexes of compounds of the formula (I) can be obtainedin a simple manner by customary processes, for example by dissolving themetal salt in alcohol, for example ethanol, and adding the solution tothe compound of the formula (I). Metal salt complexes can be isolated ina known manner, for example by filtration, and, if required, be purifiedby recrystallization.

Salts of the intermediates can also be prepared according to theprocesses mentioned above for the salts of compounds of formula (I).

N-oxides of compounds of the formula (I) or intermediates thereof can beobtained in a simple manner by customary processes, for example byN-oxidation with hydrogen peroxide (H₂02), peracids, for example peroxysulfuric acid or peroxy carboxylic acids, such asmeta-chloroperoxybenzoic acid or peroxymonosulfuric acid (Caro's acid).

Methods and Uses

The invention also relates to a method for controlling unwantedmicroorganisms, characterized in that the compounds of the formula (I)are applied to the microorganisms and/or in their habitat.

The invention further relates to seed which has been treated with atleast one compound of the formula (I).

The invention finally provides a method for protecting seed againstunwanted microorganisms by using seed treated with at least one compoundof the formula (I).

The compounds of the formula (I) have potent microbicidal activity andcan be used for control of unwanted microorganisms, such as fungi andbacteria, in crop protection and in the protection of materials.

The compounds of the formula (I) have very good fungicidal propertiesand can be used in crop protection, for example for control ofPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop protection, for example, for control ofPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

The compounds of the formula (I) can be used for curative or protectivecontrol of phytopathogenic fungi. The invention therefore also relatesto curative and protective methods for controlling phytopathogenic fungiby the use of the inventive active ingredients or compositions, whichare applied to the seed, the plant or plant parts, the fruit or the soilin which the plants grow.

Plants

All plants and plant parts can be treated in accordance with theinvention. Plants are understood here to mean all plants and plantpopulations, such as desired and undesired wild plants or crop plants(including naturally occurring crop plants). Crop plants may be plantswhich can be obtained by conventional breeding and optimization methodsor by biotechnological and genetic engineering methods or combinationsof these methods, including the transgenic plants and including theplant cultivars which are protectable and non-protectable by plantbreeders' rights. Plant parts are understood to mean all parts andorgans of plants above and below the ground, such as shoot, leaf, flowerand root, examples of which include leaves, needles, stalks, stems,flowers, fruit bodies, fruits and seeds, and also roots, tubers andrhizomes. The plant parts also include harvested material and vegetativeand generative propagation material, for example cuttings, tubers,rhizomes, slips and seeds.

Plants which can be treated in accordance with the invention include thefollowing: cotton, flax, grapevine, fruit, vegetables, such as Rosaceaesp. (for example pome fruits such as apples and pears, but also stonefruits such as apricots, cherries, almonds and peaches, and soft fruitssuch as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceaesp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana treesand plantations), Rubiaceae sp. (for example coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for example lemons, oranges andgrapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp.,Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp.,Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceaesp. (for example leek, onion), Papilionaceae sp. (for example peas);major crop plants, such as Gramineae sp. (for example maize, turf,cereals such as wheat, rye, rice, barley, oats, millet and triticale),Asteraceae sp. (for example sunflower), Brassicaceae sp. (for examplewhite cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pakchoi, kohlrabi, radishes, and oilseed rape, mustard, horseradish andcress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (forexample soya bean), Solanaceae sp. (for example potatoes),Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard,beetroot); useful plants and ornamental plants for gardens and woodedareas; and genetically modified varieties of each of these plants.

Pathogens

Non-limiting examples of pathogens of fungal diseases which can betreated in accordance with the invention include:

diseases caused by powdery mildew pathogens, for example Blumeriaspecies, for example Blumeria graminis; Podosphaera species, for examplePodosphaera leucotricha; Sphaerotheca species, for example Sphaerothecafuliginea; Uncinula species, for example Uncinula necator;diseases caused by rust disease pathogens, for example Gymnosporangiumspecies, for example Gymnosporangium sabinae; Hemileia species, forexample Hemileia vastatrix; Phakopsora species, for example Phakopsorapachyrhizi or Phakopsora meibomiae; Puccinia species, for examplePuccinia recondita, Puccinia graminis oder Puccinia striiformis;Uromyces species, for example Uromyces appendiculatus;diseases caused by pathogens from the group of the Oomycetes, forexample Albugo species, for example Albugo candida; Bremia species, forexample Bremia lactucae; Peronospora species, for example Peronosporapisi or P. brassicae; Phytophthora species, for example Phytophthorainfestans; Plasmopara species, for example Plasmopara viticola;Pseudoperonospora species, for example Pseudoperonospora humuli orPseudoperonospora cubensis; Pythium species, for example Pythiumultimum;leaf blotch diseases and leaf wilt diseases caused, for example, byAlternaria species, for example Alternaria solani; Cercospora species,for example Cercospora beticola; Cladiosporium species, for exampleCladiosporium cucumerinum; Cochliobolus species, for exampleCochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium)or Cochliobolus miyabeanus; Colletotrichum species, for exampleColletotrichum lindemuthanium; Cycloconium species, for exampleCycloconium oleaginum; Diaporthe species, for example Diaporthe citri;Elsinoe species, for example Elsinoe fawcettii; Gloeosporium species,for example Gloeosporium laeticolor; Glomerella species, for exampleGlomerella cingulata; Guignardia species, for example Guignardiabidwelli; Leptosphaeria species, for example Leptosphaeria maculans;Magnaporthe species, for example Magnaporthe grisea; Microdochiumspecies, for example Microdochium nivale; Mycosphaerella species, forexample Mycosphaerella graminicola, Mycosphaerella arachidicola orMycosphaerella fijiensis; Phaeosphaeria species, for examplePhaeosphaeria nodorum; Pyrenophora species, for example Pyrenophorateres or Pyrenophora tritici repentis; Ramularia species, for exampleRamularia collo-cygni or Ramularia areola; Rhynchosporium species, forexample Rhynchosporium secalis; Septoria species, for example Septoriaapii or Septoria lycopersici; Stagonospora species, for exampleStagonospora nodorum; Typhula species, for example Typhula incarnata;Venturia species, for example Venturia inaequalis;root and stem diseases caused, for example, by Corticium species, forexample Corticium graminearum; Fusarium species, for example Fusariumoxysporum; Gaeumannomyces species, for example Gaeumannomyces graminis;Plasmodiophora species, for example Plasmodiophora brassicae;Rhizoctonia species, for example Rhizoctonia solani; Sarocladiumspecies, for example Sarocladium oryzae; Sclerotium species, for exampleSclerotium oryzae; Tapesia species, for example Tapesia acuformis;Thielaviopsis species, for example Thielaviopsis basicola;ear and panicle diseases (including corn cobs) caused, for example, byAlternaria species, for example Alternaria spp.; Aspergillus species,for example Aspergillus flavus; Cladosporium species, for exampleCladosporium cladosporioides; Claviceps species, for example Clavicepspurpurea; Fusarium species, for example Fusarium culmomm; Gibberellaspecies, for example Gibberella zeae; Monographella species, for exampleMonographella nivalis; Stagnospora species, for example Stagnosporanodorum;diseases caused by smut fungi, for example Sphacelotheca species, forexample Sphacelotheca reiliana; Tilletia species, for example Tilletiacaries or Tilletia controversa; Urocystis species, for example Urocystisocculta; Ustilago species, for example Ustilago nuda;fruit rot caused, for example, by Aspergillus species, for exampleAspergillus flavus; Botrytis species, for example Botrytis cinerea;Penicillium species, for example Penicillium expansum or Penicilliumpurpurogenum; Rhizopus species, for example Rhizopus stolonifer;Sclerotinia species, for example Sclerotinia sclerotiomm; Verticiliumspecies, for example Verticilium alboatrum;seed- and soil-borne rot and wilt diseases, and also diseases ofseedlings, caused, for example, by Alternaria species, for exampleAlternaria brassicicola; Aphanomyces species, for example Aphanomyceseuteiches; Ascochyta species, for example Ascochyta lentis; Aspergillusspecies, for example Aspergillus flavus; Cladosporium species, forexample Cladosporium herbarum; Cochliobolus species, for exampleCochliobolus sativus (conidial form: Drechslera, Bipolaris Syn:Helminthosporium); Colletotrichum species, for example Colletotrichumcoccodes; Fusarium species, for example Fusarium culmorum; Gibberellaspecies, for example Gibberella zeae; Macrophomina species, for exampleMacrophomina phaseolina; Microdochium species, for example Microdochiumnivale; Monographella species, for example Monographella nivalis;Penicillium species, for example Penicillium expansum; Phoma species,for example Phoma lingam; Phomopsis species, for example Phomopsissojae; Phytophthora species, for example Phytophthora cactorum;Pyrenophora species, for example Pyrenophora graminea; Pyriculariaspecies, for example Pyricularia oryzae; Pythium species, for examplePythium ultimum; Rhizoctonia species, for example Rhizoctonia solani;Rhizopus species, for example Rhizopus oryzae; Sclerotium species, forexample Sclerotium rolfsii; Septoria species, for example Septorianodorumn; Typhula species, for example Typhula incarnata; Verticilliumspecies, for example Verticillium dahliae;cancers, galls and witches' broom caused, for example, by Nectriaspecies, for example Nectria galligena; wilt diseases caused, forexample, by Monilinia species, for example Monilinia laxa;deformations of leaves, flowers and fruits caused, for example, byExobasidium species, for example Exobasidium vexans; Taphrina species,for example Taphrina deformans;degenerative diseases in woody plants, caused, for example, by Escaspecies, for example Phaeomoniella chlamydospora, Phaeoacremoniumaleophilum or Fomitiporia mediterranea; Ganoderma species, for exampleGanoderma boninense;diseases of flowers and seeds caused, for example, by Botrytis species,for example Botrytis cinerea;diseases of plant tubers caused, for example, by Rhizoctonia species,for example Rhizoctonia solani; Helminthosporium species, for exampleHelminthosporium solani;diseases caused by bacterial pathogens, for example Xanthomonas species,for example Xanthomonas campestris pv. olyzae; Pseudomonas species, forexample Pseudomonas syringae pv. lachrymans; Erwinia species, forexample Erwinia amylovora.

Preference is given to controlling the following diseases of soya beans:

Fungal diseases on leaves, stems, pods and seeds caused, for example, byAlternaria leaf spot (Alternaria spec. atrans tenuissima), Anthracnose(Colletotrichum gloeosporoides dematium var. tmrncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaemrlina trifolii), phyllostica leaf spot (Phyllostictasojaecola), pod and stem blight (Phomopsis sojae), powdery mildew(Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines),rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust(Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphacelomaglycines), stemphylium leaf blight (Stemphylium botyosum), target spot(Coynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by blackroot rot (Calonectria crotalariae), charcoal rot (Macrophominaphaseolina), fusarium blight or wilt, root rot, and pod and collar rot(Fusarium oxysporun, Fusarium orthoceras, Fusarium semitectum, Fusariumequiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris),neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthephaseolorum), stem canker (Diaporthe phaseolomm var. caulivora),phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophoragregata), pythium rot (Pythium aphanidermatum, Pythium irregulare,Pythium debayanum, Pythium myriotylum, Pythium ultimum), rhizoctoniaroot rot, stem decay, and damping-off (Rhizoctonia solani), sclerotiniastem decay (Sclerotinia sclerotioummn), sclerotinia southern blight(Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

Plant Growth Regulation

In some cases, the compounds of the formula (I) can, at particularconcentrations or application rates, also be used as growth regulatorsor agents to improve plant properties, or as microbicides, for exampleas fungicides, antimycotics, bactericides, viricides (includingcompositions against viroids) or as compositions against MLO(Mycoplasma-like organisms) and RLO (Rickettsia-like organisms).

The compounds of the formula (I) intervene in physiological processes ofplants and can therefore also be used as plant growth regulators. Plantgrowth regulators may exert various effects on plants. The effect of thesubstances depends essentially on the time of application in relation tothe developmental stage of the plant, and also on the amounts of activeingredient applied to the plants or their environment and on the type ofapplication. In each case, growth regulators should have a particulardesired effect on the crop plants.

Growth regulating effects, comprise earlier germination, betteremergence, more developed root system and/or improved root growth,increased ability of tillering, more productive tillers, earlierflowering, increased plant height and/or biomass, shorting of stems,improvements in shoot growth, number of kernels/ear, number of ears/m²,number of stolons and/or number of flowers, enhanced harvest index,bigger leaves, less dead basal leaves, improved phyllotaxy, earliermaturation/earlier fruit finish, homogenous riping, increased durationof grain filling, better fruit finish, bigger fruit/vegetable size,sprouting resistance and reduced lodging.

Increased or improved yield is referring to total biomass per hectare,yield per hectare, kernel/fruit weight, seed size and/or hectolitreweight as well as to improved product quality, comprising:

improved processability relating to size distribution (kernel, fruit,etc.), homogenous riping, grain moisture, better milling, bettervinification, better brewing, increased juice yield, harvestability,digestibility, sedimentation value, falling number, pod stability,storage stability, improved fiber length/strength/uniformity, increaseof milk and/or meet quality of silage fed animals, adaptation to cookingand frying;further comprising improved marketability relating to improvedfruit/grain quality, size distribution (kernel, fruit, etc.), increasedstorage/shelf-life, firmness/softness, taste (aroma, texture, etc.),grade (size, shape, number of berries, etc.), number of berries/fruitsper bunch, crispness, freshness, coverage with wax, frequency ofphysiological disorders, colour, etc.;further comprising increased desired ingredients such as e.g. proteincontent, fatty acids, oil content, oil quality, aminoacid composition,sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols,starch content, nutritional quality, gluten content/index, energycontent, taste, etc.;and further comprising decreased undesired ingredients such as e.g. lessmycotoxines, less aflatoxins, geosmin level, phenolic aromas, lacchase,polyphenol oxidases and peroxidases, nitrate content etc.

Plant growth-regulating compounds can be used, for example, to slow downthe vegetative growth of the plants. Such growth depression is ofeconomic interest, for example, in the case of grasses, since it is thuspossible to reduce the frequency of grass cutting in ornamental gardens,parks and sport facilities, on roadsides, at airports or in fruit crops.Also of significance is the inhibition of the growth of herbaceous andwoody plants on roadsides and in the vicinity of pipelines or overheadcables, or quite generally in areas where vigorous plant growth isunwanted.

Also important is the use of growth regulators for inhibition of thelongitudinal growth of cereal. This reduces or completely eliminates therisk of lodging of the plants prior to harvest. In addition, growthregulators in the case of cereals can strengthen the culm, which alsocounteracts lodging. The employment of growth regulators for shorteningand strengthening culms allows the deployment of higher fertilizervolumes to increase the yield, without any risk of lodging of the cerealcrop.

In many crop plants, vegetative growth depression allows denserplanting, and it is thus possible to achieve higher yields based on thesoil surface. Another advantage of the smaller plants obtained in thisway is that the crop is easier to cultivate and harvest.

Reduction of the vegetative plant growth may also lead to increased orimproved yields because the nutrients and assimilates are of morebenefit to flower and fruit formation than to the vegetative parts ofthe plants.

Alternatively, growth regulators can also be used to promote vegetativegrowth. This is of great benefit when harvesting the vegetative plantparts. However, promoting vegetative growth may also promote generativegrowth in that more assimilates are formed, resulting in more or largerfruits.

Furthermore, beneficial effects on growth or yield can be achievedthrough improved nutrient use efficiency, especially nitrogen (N)-useefficiency, phosphorus (P)-use efficiency, water use efficiency,improved transpiration, respiration and/or CO2 assimilation rate, betternodulation, improved Ca-metabolism etc.

Likewise, growth regulators can be used to alter the composition of theplants, which in turn may result in an improvement in quality of theharvested products. Under the influence of growth regulators,parthenocarpic fruits may be formed. In addition, it is possible toinfluence the sex of the flowers. It is also possible to produce sterilepollen, which is of great importance in the breeding and production ofhybrid seed.

Use of growth regulators can control the branching of the plants. On theone hand, by breaking apical dominance, it is possible to promote thedevelopment of side shoots, which may be highly desirable particularlyin the cultivation of ornamental plants, also in combination with aninhibition of growth. On the other hand, however, it is also possible toinhibit the growth of the side shoots. This effect is of particularinterest, for example, in the cultivation of tobacco or in thecultivation of tomatoes.

Under the influence of growth regulators, the amount of leaves on theplants can be controlled such that defoliation of the plants is achievedat a desired time. Such defoliation plays a major role in the mechanicalharvesting of cotton, but is also of interest for facilitatingharvesting in other crops, for example in viticulture. Defoliation ofthe plants can also be undertaken to lower the transpiration of theplants before they are transplanted.

Furthermore, growth regulators can modulate plant senescence, which mayresult in prolonged green leaf area duration, a longer grain fillingphase, improved yield quality, etc.

Growth regulators can likewise be used to regulate fruit dehiscence. Onthe one hand, it is possible to prevent premature fruit dehiscence. Onthe other hand, it is also possible to promote fruit dehiscence or evenflower abortion to achieve a desired mass (“thinning”). In addition itis possible to use growth regulators at the time of harvest to reducethe forces required to detach the fruits, in order to allow mechanicalharvesting or to facilitate manual harvesting.

Growth regulators can also be used to achieve faster or else delayedripening of the harvested material before or after harvest. This isparticularly advantageous as it allows optimal adjustment to therequirements of the market. Moreover, growth regulators in some casescan improve the fruit colour. In addition, growth regulators can also beused to synchronize maturation within a certain period of time. Thisestablishes the prerequisites for complete mechanical or manualharvesting in a single operation, for example in the case of tobacco,tomatoes or coffee.

By using growth regulators, it is additionally possible to influence theresting of seed or buds of the plants, such that plants such aspineapple or ornamental plants in nurseries, for example, germinate,sprout or flower at a time when they are normally not inclined to do so.In areas where there is a risk of frost, it may be desirable to delaybudding or germination of seeds with the aid of growth regulators, inorder to avoid damage resulting from late frosts.

Finally, growth regulators can induce resistance of the plants to frost,drought or high salinity of the soil. This allows the cultivation ofplants in regions which are normally unsuitable for this purpose.

Resistance Induction/Plant Health and Other Effects

The compounds of the formula (I) also exhibit a potent strengtheningeffect in plants. Accordingly, they can be used for mobilizing thedefences of the plant against attack by undesirable microorganisms.

Plant-strengthening (resistance-inducing) substances in the presentcontext are substances capable of stimulating the defence system ofplants in such a way that the treated plants, when subsequentlyinoculated with undesirable microorganisms, develop a high degree ofresistance to these microorganisms.

Further, in context with the present invention plant physiology effectscomprise the following:

Abiotic stress tolerance, comprising tolerance to high or lowtemperatures, drought tolerance and recovery after drought stress, wateruse efficiency (correlating to reduced water consumption), floodtolerance, ozone stress and UV tolerance, tolerance towards chemicalslike heavy metals, salts, pesticides etc.

Biotic stress tolerance, comprising increased fungal resistance andincreased resistance against nematodes, viruses and bacteria. In contextwith the present invention, biotic stress tolerance preferably comprisesincreased fungal resistance and increased resistance against nematodes.

Increased plant vigor, comprising plant health/plant quality and seedvigor, reduced stand failure, improved appearance, increased recoveryafter periods of stress, improved pigmentation (e.g. chlorophyllcontent, stay-green effects, etc.) and improved photosyntheticefficiency.

Mycotoxins

In addition, the compounds of the formula (I) can reduce the mycotoxincontent in the harvested material and the foods and feeds preparedtherefrom. Mycotoxins include particularly, but not exclusively, thefollowing: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- andHT2-toxin, fumonisins, zearalenon, moniliformin, fusarin,diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin,fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins whichcan be produced, for example, by the following fungi: Fusarium spec.,such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F.culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. ifjikoroi,F. musarum, F. oxysporum, F. proliferatum, F. poae, F.pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani,F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F.verticillioides etc., and also by Aspergillus spec., such as A. flavus,A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A.versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P.citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec.,such as C. purpurea, C. fisiformis, C. paspali, C. africana,Stachybotrys spec. and others.

Material Protection

The compounds of the formula (I) can also be used in the protection ofmaterials, for protection of industrial materials against attack anddestruction by phytopathogenic fungi.

In addition, the compounds of the formula (I) can be used as antifoulingcompositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to meaninanimate materials which have been prepared for use in industry. Forexample, industrial materials which are to be protected by inventivecompositions from microbial alteration or destruction may be adhesives,glues, paper, wallpaper and board/cardboard, textiles, carpets, leather,wood, fibers and tissues, paints and plastic articles, coolinglubricants and other materials which can be infected with or destroyedby microorganisms. Parts of production plants and buildings, for examplecooling-water circuits, cooling and heating systems and ventilation andair-conditioning units, which may be impaired by the proliferation ofmicroorganisms may also be mentioned within the scope of the materialsto be protected. Industrial materials within the scope of the presentinvention preferably include adhesives, sizes, paper and card, leather,wood, paints, cooling lubricants and heat transfer fluids, morepreferably wood.

The compounds of the formula (I) may prevent adverse effects, such asrotting, decay, discoloration, decoloration or formation of mould.

In the case of treatment of wood the compounds of the formula (I) mayalso be used against fungal diseases liable to grow on or inside timber.The term “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting acomposition according to the invention; this includes for example directapplication, spraying, dipping, injection or any other suitable means.

In addition, the compounds of the formula (I) can be used to protectobjects which come into contact with saltwater or brackish water,especially hulls, screens, nets, buildings, moorings and signallingsystems, from fouling.

The compounds of the formula (I) can also be employed for protectingstorage goods. Storage goods are understood to mean natural substancesof vegetable or animal origin or processed products thereof which are ofnatural origin, and for which long-term protection is desired. Storagegoods of vegetable origin, for example plants or plant parts, such asstems, leaves, tubers, seeds, fruits, grains, can be protected freshlyharvested or after processing by (pre)dying, moistening, comminuting,grinding, pressing or roasting. Storage goods also include timber, bothunprocessed, such as construction timber, electricity poles andbarriers, or in the form of finished products, such as furniture.Storage goods of animal origin are, for example, hides, leather, fursand hairs. The inventive compositions may prevent adverse effects, suchas rotting, decay, discoloration, decoloration or formation of mould.

Microorganisms capable of degrading or altering the industrial materialsinclude, for example, bacteria, fungi, yeasts, algae and slimeorganisms. The compounds of the formula (I) preferably act againstfungi, especially moulds, wood-discoloring and wood-destroying fungi(Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), andagainst slime organisms and algae. Examples include microorganisms ofthe following genera: Alternaria, such as Alternaria tenuis;Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomiumglobosum; Coniophora, such as Coniophora puetana; Lentinus, such asLentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus,such as Polyporus versicolor; Aureobasidium, such as Aureobasidiumpullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma,such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicolaspp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp.,Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp.,Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such asEscherichia coli; Pseudomonas, such as Pseudomonas aeruginosa;Staphylococcus, such as Staphylococcus aureus, Candida spp. andSaccharomyces spp., such as Saccharomyces cerevisae.

Formulations

The present invention further relates to a composition for controllingunwanted microorganisms, comprising at least one of the compounds of theformula (I). These are preferably fungicidal compositions which compriseagriculturally suitable auxiliaries, solvents, carriers, surfactants orextenders.

According to the invention, a carrier is a natural or synthetic, organicor inorganic substance with which the active ingredients are mixed orcombined for better applicability, in particular for application toplants or plant parts or seed. The carrier, which may be solid orliquid, is generally inert and should be suitable for use inagriculture.

Useful solid carriers include: for example ammonium salts and naturalrock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite,montmorillonite or diatomaceous earth, and synthetic rock flours, suchas finely divided silica, alumina and silicates; useful solid carriersfor granules include: for example, crushed and fractionated naturalrocks such as calcite, marble, pumice, sepiolite and dolomite, and alsosynthetic granules of inorganic and organic flours, and granules oforganic material such as paper, sawdust, coconut shells, maize cobs andtobacco stalks; useful emulsifiers and/or foam-formers include: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; suitable dispersants are nonionic and/orionic substances, for example from the classes of the alcohol-POE and/or-POP ethers, acid and/or POP POE esters, alkylaryl and/or POP POEethers, fat and/or POP POE adducts, POE- and/or POP-polyol derivatives,POE- and/or POP-sorbitan or -sugar adducts, alkyl or aryl sulphates,alkyl- or arylsulphonates and alkyl or aryl phosphates or thecorresponding PO-ether adducts. Additionally suitable are oligo- orpolymers, for example those derived from vinylic monomers, from acrylicacid, from EO and/or PO alone or in combination with, for example,(poly)alcohols or (poly)amines. It is also possible to use lignin andits sulphonic acid derivatives, unmodified and modified celluloses,aromatic and/or aliphatic sulphonic acids and also their adducts withformaldehyde.

The active ingredients can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspoemulsion concentrates, natural productsimpregnated with active ingredient, synthetic substances impregnatedwith active ingredient, fertilizers and also microencapsulations inpolymeric substances.

The active ingredients can be applied as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsions, water- or oil-based suspensions, powders, wettablepowders, pastes, soluble powders, dusts, soluble granules, granules forbroadcasting, suspoemulsion concentrates, natural products impregnatedwith active ingredient, synthetic substances impregnated with activeingredient, fertilizers and also microencapsulations in polymericsubstances. Application is accomplished in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading-on and the like. It is also possible to deploy theactive ingredients by the ultra-low volume method or to inject theactive ingredient preparation/the active ingredient itself into thesoil. It is also possible to treat the seed of the plants.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active ingredients with at least one customaryextender, solvent or diluent, emulsifier, dispersant and/or binder orfixing agent, wetting agent, a water repellent, if appropriatesiccatives and UV stabilizers and if appropriate dyes and pigments,antifoams, preservatives, secondary thickeners, stickers, gibberellinsand also other processing auxiliaries.

The present invention includes not only formulations which are alreadyready for use and can be deployed with a suitable apparatus to the plantor the seed, but also commercial concentrates which have to be dilutedwith water prior to use.

The compounds of the formula (I) may be present as such or in their(commercial) formulations and in the use forms prepared from theseformulations as a mixture with other (known) active ingredients, such asinsecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, fertilizers,safeners and/or semiochemicals.

The auxiliaries used may be those substances which are suitable forimparting particular properties to the composition itself or and/or topreparations derived therefrom (for example spray liquors, seeddressings), such as certain technical properties and/or also particularbiological properties. Typical auxiliaries include: extenders, solventsand carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnonaromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which mayoptionally also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

Liquefied gaseous extenders or carriers are understood to mean liquidswhich are gaseous at standard temperature and under standard pressure,for example aerosol propellants such as halohydrocarbons, or elsebutane, propane, nitrogen and carbon dioxide.

In the formulations it is possible to use tackifiers such ascarboxymethylcellulose, natural and synthetic polymers in the form ofpowders, granules or latices, such as gum arabic, polyvinyl alcohol andpolyvinyl acetate, or else natural phospholipids such as cephalins andlecithins and synthetic phospholipids. Further additives may be mineraland vegetable oils.

If the extender used is water, it is also possible to use, for example,organic solvents as auxiliary solvents. Useful liquid solvents areessentially: aromatics such as xylene, toluene or alkylnaphthalenes,chlorinated aromatics or chlorinated aliphatic hydrocarbons such aschlorobenzenes, chloroethylenes or methylene chloride, aliphatichydrocarbons such as cyclohexane or paraffins, for example petroleumfractions, alcohols such as butanol or glycol and their ethers andesters, ketones such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents such asdimethylformamide and dimethyl sulphoxide, or else water.

Compositions comprising compounds of the formula (I) may additionallycomprise further components, for example surfactants. Suitablesurfactants are emulsifiers and/or foam formers, dispersants or wettingagents having ionic or nonionic properties, or mixtures of thesesurfactants. Examples thereof are salts of polyacrylic acid, salts oflignosulphonic acid, salts of phenolsulphonic acid ornaphthalenesulphonic acid, polycondensates of ethylene oxide with fattyalcohols or with fatty acids or with fatty amines, substituted phenols(preferably alkylphenols or arylphenols), salts of sulphosuccinicesters, taurine derivatives (preferably alkyl taurates), phosphoricesters of polyethoxylated alcohols or phenols, fatty esters of polyols,and derivatives of the compounds containing sulphates, sulphonates andphosphates, for example alkylaryl polyglycol ethers, alkylsulphonates,alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphitewaste liquors and methylcellulose. The presence of a surfactant isnecessary if one of the active ingredients and/or one of the inertcarriers is insoluble in water and when application is effected inwater. The proportion of surfactants is between 5 and 40 percent byweight of the inventive composition.

It is possible to use dyes such as inorganic pigments, for example ironoxide, titanium oxide and Prussian Blue, and organic dyes such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

Further additives may be perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Additional components may be stabilizers, such as cold stabilizers,preservatives, antioxidants, light stabilizers, or other agents whichimprove chemical and/or physical stability.

If appropriate, other additional components may also be present, forexample protective colloids, binders, adhesives, thickeners, thixotropicsubstances, penetrants, stabilizers, sequestering agents, complexformers.

In general, the active ingredients can be combined with any solid orliquid additive commonly used for formulation purposes.

The formulations contain generally between 0.05 and 99% by weight, 0.01and 98% by weight, preferably between 0.1 and 95% by weight, morepreferably between 0.5 and 90% of active ingredient, most preferablybetween 10 and 70 percent by weight.

The formulations described above can be used for controlling unwantedmicroorganisms, in which the compositions comprising compounds of theformula (I) are applied to the microorganisms and/or in their habitat.

Mixtures

Compounds of the formula (I) can be used as such or in formulationsthereof and can be mixed with known fungicides, bactericides,acaricides, nematicides or insecticides, in order thus to broaden, forexample, the activity spectrum or to prevent development of resistance.

Useful mixing partners include, for example, known fungicides,insecticides, acaricides, nematicides or else bactericides (see alsoPesticide Manual, 14th ed.).

A mixture with other known active ingredients, such as herbicides, orwith fertilizers and growth regulators, safeners and/or semiochemicals,is also possible.

Hence, the invention further relates to mixtures and formulations,comprising at least one compound of formula (I) and at least a furtheractive compound, preferably selected from fungicides, bactericides,acaricides, nematicides, insecticides, herbicides, fertilizers, growthregulators, safeners and/or semiochemicals, more preferably fromfungicides, insecticides, herbicides, growth regulators and/or safeners,most preferably from fungicides.

Preferably the at least one further active compound is a fungicideselected from the following groups

-   -   (1) inhibitors of the ergosterol synthesis,    -   (2) inhibitors of the respiratory chain at complex I or II,    -   (3) inhibitors of the respiratory chain at complex III,    -   (4) inhibitors of the mitosis and cell division,    -   (5) compounds capable of having a multisite action,    -   (6) compounds capable of inducing a host defense,    -   (7) inhibitors of the amino acid and/or protein biosynthesis,    -   (8) inhibitors of the ATP production,    -   (9) inhibitors of the cell wall synthesis,    -   (10) inhibitors of the lipid and membrane synthesis,    -   (11) inhibitors of the melanine biosynthesis,    -   (12) inhibitors of the nucleic acid synthesis,    -   (13) inhibitors of the signal transduction,    -   (14) compounds capable of acting as uncoupler,    -   (15) other fungicides.

More preferably the at least one further active compound is selectedfrom the group consisting of (1.001) cyproconazole, (1.002)difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005)fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008)fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalilsulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil,(1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole,(1.018) prothioconazole, (1.019) Pyrisoxazole, (1.020) spiroxamine,(1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol,(1.024) tridemorph, (1.025) triticonazole, (1.026)(1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.027)(1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.028)(2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.029)(2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.030)(2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.031)(2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.032)(2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.033)(2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.034)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.035)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.036)[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol,(1.037)1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.038)1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole,(1.039)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.040)1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.041)1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate, (1.042)2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.043)2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.044)2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.045)2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.046)2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.047)2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.049)2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.050)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.051)2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.052)2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol,(1.054)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol,(1.055)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol,(1.056)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.057)2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione,(1.059)5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol,(1.060)5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.061)5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole,(1.063)N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.064)N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.065)N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.066)N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide,(1.067)N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.068)N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.069)N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.070)N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide,(1.071)N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide,(1.072)N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.073)N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide,(1.074)N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide,(1.075)N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide,(1.076)N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.077)N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.078)N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.079)N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080)N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide,(1.081) Mefentrifluconazole, (1.082) Ipfentrifluconazole, (2.001)benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin,(2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008)furametpyr, (2.009) Isofetamid, (2.010) isopyrazam (anti-epimericenantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR),(2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS andanti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimericenantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS),(2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020)Pyraziflumid, (2.021) sedaxane, (2.022)1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.023)1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.024)1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.025)1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide,(2.026)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide,(2.027)3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide,(2.028)3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.029)3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide,(2.030)3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,(2.031)3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.032)3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide,(2.033)5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine,(2.034)N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.035)N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.036)N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.037)N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.038)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.039)N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.040)N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.041)N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.042)N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.043)N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.044)N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.045)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide,(2.046)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.047)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.048)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide,(2.049)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.050)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,(2.051)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.052)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.053)N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.054)N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.055)N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(2.056)N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,(3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004)coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007)dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010)fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013)kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016)picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019)pyraoxystrobin, (3.020) trifloxystrobin, (3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,(3.022)(2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.023)(2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.024)(2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.025)(3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl2-methylpropanoate, (3.026)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide,(3.027)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide,(3.028)(2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide,(3.029) methyl{5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate,(4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004)fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007)thiophanate-methyl, (4.008) zoxamide, (4.009)3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010)3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,(4.011)3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine,(4.012)4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.013)4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.014)4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.015)4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.016)4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.017)4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.018)4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.019)4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.020)4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.021)4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.022)4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,(4.023)N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.024)N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine,(4.025)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.(5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004)chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate,(5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2+)sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013)mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017)oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparationsincluding calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022)ziram, (5.023)6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile, (6.001) acibenzolar-S-methyl, (6.002)isotianil, (6.003) probenazole, (6.004) tiadinil, (7.001) cyprodinil,(7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004)oxytetracycline, (7.005) pyrimethanil, (7.006)3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone,(8.001) silthiofam, (9.001) benthiavalicarb, (9.002) dimethomorph,(9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006)pyrimorph, (9.007) valifenalate, (9.008)(2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(9.009)(2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one,(10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003)tolclofos-methyl, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate, (12.001)benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl,(12.004) metalaxyl-M (mefenoxam), (13.001) fludioxonil, (13.002)iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005)quinoxyfen, (13.006) vinclozolin, (14.001) fluazinam, (14.002)meptyldinocap, (15.001) Abscisic acid, (15.002) benthiazole, (15.003)bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006)chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009)cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012)fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium,(15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017)mildiomycin, (15.018) natamycin, (15.019) nickeldimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021)oxamocarb, (15.022) Oxathiapiprolin, (15.023) oxyfenthiin, (15.024)pentachlorophenol and salts, (15.025) phosphorous acid and its salts,(15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone),(15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide,(15.031)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.032)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone,(15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034)2,6-dimethyl−1H,5H-[1,4]dithiino[2,3-c:5,6-c′]dipyrrole-1,3,5,7(2H,6H)-tetrone,(15.035)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.036)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.037)2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone,(15.038)2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline,(15.039)2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.040)2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.041)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol,(15.042)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol,(15.043)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (15.044)2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenylmethanesulfonate, (15.045) 2-phenylphenol and salts, (15.046)3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.047)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline,(15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form:4-amino-5-fluoropyrimidin-2(1H)-one), (15.049)4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050)5-amino-1,3,4-thiadiazole-2-thiol, (15.051)5-chloro-N′-phenyl-N′X-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide,(15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053)5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine,(15.055) but-3-yn-1-yl{6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,(15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057)phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate,(15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061)tert-butyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate,and (15.062)5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one.

Seed Treatment

The invention furthermore includes a method for treating seed.

A further aspect of the present invention relates in particular to seeds(dormant, primed, pregerminated or even with emerged roots and leaves)treated with at least one of the compounds of the formula (I). Theinventive seeds are used in methods for protection of seeds and emergedplants from the seeds from phytopathogenic harmful fungi. In thesemethods, seed treated with at least one inventive active ingredient isused.

The compounds of the formula (I) are also suitable for the treatment ofseeds and young seedlings. A large part of the damage to crop plantscaused by harmful organisms is triggered by the infection of the seedsbefore sowing or after germination of the plant. This phase isparticularly critical since the roots and shoots of the growing plantare particularly sensitive, and even small damage may result in thedeath of the plant. Accordingly, there is great interest in protectingthe seed and the germinating plant by using appropriate compositions.

It is also desirable to optimize the amount of the active ingredientused so as to provide the best possible protection for the seeds, thegerminating plants and emerged seedlings from attack by phytopathogenicfungi, but without damaging the plants themselves by the activeingredient used. In particular, methods for the treatment of seed shouldalso take into consideration the intrinsic phenotypes of transgenicplants in order to achieve optimum protection of the seed and thegerminating plant with a minimum of crop protection compositions beingemployed.

The present invention therefore also relates to a method for protectingseeds, germinating plants and emerged seedlings against attack by animalpests and/or phytopathogenic harmful microorganisms by treating theseeds with an inventive composition. The invention also relates to theuse of the compositions according to the invention for treating seedsfor protecting the seeds, the germinating plants and emerged seedlingsagainst animal pests and/or phytopathogenic microorganisms. Theinvention further relates to seeds which has been treated with aninventive composition for protection from animal pests and/orphytopathogenic microorganisms.

One of the advantages of the present invention is that the treatment ofthe seeds with these compositions not only protects the seed itself, butalso the resulting plants after emergence, from animal pests and/orphytopathogenic harmful microorganisms. In this way, the immediatetreatment of the crop at the time of sowing or shortly thereafterprotect plants as well as seed treatment in prior to sowing. It islikewise considered to be advantageous that the inventive activeingredients or compositions can be used especially also for transgenicseed, in which case the plant which grows from this seed is capable ofexpressing a protein which acts against pests, herbicidal damage orabiotic stress. The treatment of such seeds with the inventive activeingredients or compositions, for example an insecticidal protein, canresult in control of certain pests. Surprisingly, a further synergisticeffect can be observed in this case, which additionally increases theeffectiveness for protection against attack by pests, microorganisms,weeds or abiotic stress.

The compounds of the formula (I) are suitable for protection of seed ofany plant variety which is used in agriculture, in the greenhouse, inforests or in horticulture. More particularly, the seed is that ofcereals (such as wheat, barley, rye, millet and oats), oilseed rape,maize, cotton, soybeen, rice, potatoes, sunflower, beans, coffee, beet(e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato,cucumber, onions and lettuce), lawns and ornamental plants. Ofparticular significance is the treatment of the seed of wheat, soybean,oilseed rape, maize and rice.

As also described below, the treatment of transgenic seed with theinventive active ingredients or compositions is of particularsignificance. This refers to the seed of plants containing at least oneheterologous gene which allows the expression of a polypeptide orprotein, e.g. having insecticidal properties. These heterologous genesin transgenic seeds may originate, for example, from microorganisms ofthe species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma,Clavibacter, Glomus or Gliocladium. These heterologous genes preferablyoriginates from Bacillus sp., in which case the gene product iseffective against the European corn borer and/or the Western cornrootworm. Particularly preferably, the heterologous genes originate fromBacillus thuringiensis.

In the context of the present invention, the inventive composition isapplied to seeds either alone or in a suitable formulation. Preferably,the seed is treated in a state in which it is sufficiently stable for nodamage to occur in the course of treatment. In general, seeds can betreated at any time between harvest and some time after sowing. It iscustomary to use seed which has been separated from the plant and freedfrom cobs, shells, stalks, coats, hairs or the flesh of the fruits. Forexample, it is possible to use seed which has been harvested, cleanedand dried down to a moisture content of less than 15% by weight.Alternatively, it is also possible to use seed which, after drying, forexample, has been treated with water and then dried again, or seeds justafter priming, or seeds stored in primed conditions or pre-germinatedseeds, or seeds sown on nursery trays, tapes or paper.

When treating the seeds, it generally has to be ensured that the amountof the inventive composition applied to the seed and/or the amount offurther additives is selected such that the germination of the seed isnot impaired, or that the resulting plant is not damaged. This must beensured particularly in the case of active ingredients which can exhibitphytotoxic effects at certain application rates.

The compounds of the formula (I) can be applied directly, i.e. withoutcontaining any other components and without having been diluted. Ingeneral, it is preferable to apply the compositions to the seed in theform of a suitable formulation. Suitable formulations and methods forseed treatment are known to those skilled in the art. The compounds ofthe formula (I) can be converted to the customary formulations relevantto on-seed applications, such as solutions, emulsions, suspensions,powders, foams, slurries or combined with other coating compositions forseed, such as film forming materials, pelleting materials, fine iron orother metal powders, granules, coating material for inactivated seeds,and also ULV formulations.

These formulations are prepared in a known manner, by mixing the activeingredients or active ingredient combinations with customary additives,for example customary extenders and solvents or diluents, dyes, wettingagents, dispersants, emulsifiers, antifoams, preservatives, secondarythickeners, adhesives, gibberellins, and also water.

Useful dyes which may be present in the seed dressing formulationsusable in accordance with the invention are all dyes which are customaryfor such purposes. It is possible to use either pigments, which aresparingly soluble in water, or dyes, which are soluble in water.Examples include the dyes known by the names Rhodamine B, C.I. PigmentRed 112 and C.I. Solvent Red 1.

Useful wetting agents which may be present in the seed dressingformulations usable in accordance with the invention are all substanceswhich promote wetting and which are conventionally used for theformulation of active agrochemical ingredients. Usable with preferenceare alkylnaphthalenesulphonates, such as diisopropyl- ordiisobutylnaphthalenesulphonates.

Useful dispersants and/or emulsifiers which may be present in the seeddressing formulations usable in accordance with the invention are allnonionic, anionic and cationic dispersants conventionally used for theformulation of active agrochemical ingredients. Usable with preferenceare nonionic or anionic dispersants or mixtures of nonionic or anionicdispersants. Useful nonionic dispersants include especially ethyleneoxide/propylene oxide block polymers, alkylphenol polyglycol ethers andtristryrylphenol polyglycol ether, and the phosphated or sulphatedderivatives thereof. Suitable anionic dispersants are especiallylignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehydecondensates.

Antifoams which may be present in the seed dressing formulations usablein accordance with the invention are all foam-inhibiting substancesconventionally used for the formulation of active agrochemicalingredients. Silicone antifoams and magnesium stearate can be used withpreference.

Preservatives which may be present in the seed dressing formulationsusable in accordance with the invention are all substances usable forsuch purposes in agrochemical compositions. Examples includedichlorophene and benzyl alcohol hemiformal.

Secondary thickeners which may be present in the seed dressingformulations usable in accordance with the invention are all substancesusable for such purposes in agrochemical compositions. Preferredexamples include cellulose derivatives, acrylic acid derivatives,xanthan, modified clays and finely divided silica.

Adhesives which may be present in the seed dressing formulations usablein accordance with the invention are all customary binders usable inseed dressing products. Preferred examples include polyvinylpyrrolidone,polyvinyl acetate, polyvinyl alcohol and tylose.

The formulations for on-seed applications usable in accordance with theinvention can be used to treat a wide variety of different kinds of seedeither directly or after prior dilution with water. For instance, theconcentrates or the preparations obtainable therefrom by dilution withwater can be used to dress the seed of cereals, such as wheat, barley,rye, oats, and triticale, and also seeds of maize, soybean, rice,oilseed rape, peas, beans, cotton, sunflowers, and beets, or else a widevariety of different vegetable seeds. The formulations usable inaccordance with the invention, or the dilute preparations thereof, canalso be used for seeds of transgenic plants. In this case, additionalsynergistic effects may also occur in interaction with the substancesformed by expression.

For treatment of seeds with the formulations usable in accordance withthe invention, or the preparations prepared therefrom by adding water,all mixing units usable customarily for on-seed applications are useful.Specifically, the procedure in on-seed applications is to place theseeds into a mixer, to add the particular desired amount of theformulations, either as such or after prior dilution with water, and tomix everything until all applied formulations are distributedhomogeneously on the seeds. If appropriate, this is followed by a dryingoperation.

The application rate of the formulations usable in accordance with theinvention can be varied within a relatively wide range. It is guided bythe particular content of the active ingredients in the formulations andby the seeds. The application rate of each single active ingredient isgenerally between 0.001 and 15 g per kilogram of seed, preferablybetween 0.01 and 5 g per kilogram of seed.

Antimycotic Effects

In addition, the compounds of the formula (I) also have very goodantimycotic effects. They have a very broad antimycotic activityspectrum, especially against dermatophytes and yeasts, moulds anddiphasic fungi (for example against Candida species, such as Candidaalbicans, Candida glabrata), and Epidermophyton floccosum, Aspergillusspecies, such as Aspergillus niger and Aspergillus fumigatus,Trichophyton species, such as Trichophyton mentagrophytes, Microsporonspecies such as Microsporon canis and audouinii. The enumeration ofthese fungi by no means constitutes a restriction of the mycoticspectrum covered, and is merely of illustrative character.

The compounds can be used also to control important fungal pathogens infish and crustacea farming, e.g. saprolegnia diclina in trouts,saprolegnia parasitica in crayfish.

The compounds of the formula (I) can therefore be used both in medicaland in non-medical applications.

The compounds of the formula (I) can be used as such, in the form oftheir formulations or the use forms prepared therefrom, such asready-to-use solutions, suspensions, wettable powders, pastes, solublepowders, dusts and granules. Application is accomplished in a customarymanner, for example by watering, spraying, atomizing, broadcasting,dusting, foaming, spreading-on and the like. It is also possible todeploy the active ingredients by the ultra-low volume method or toinject the active ingredient preparation/the active ingredient itselfinto the soil. It is also possible to treat the seed of the plants.

GMO

As already mentioned above, it is possible to treat all plants and theirparts in accordance with the invention. In a preferred embodiment, wildplant species and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andalso parts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts” or “parts of plants” or “plant parts” have been explainedabove. More preferably, plants of the plant cultivars which arecommercially available or are in use are treated in accordance with theinvention. Plant cultivars are understood to mean plants which have newproperties (“traits”) and have been obtained by conventional breeding,by mutagenesis or by recombinant DNA techniques. They can be cultivars,varieties, bio- or genotypes.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants ofwhich a heterologous gene has been stably integrated into genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, cosuppression technology, RNAinterference—RNAi—technology or microRNA—miRNA—technology). Aheterologous gene that is located in the genome is also called atransgene. A transgene that is defined by its particular location in theplant genome is called a transformation or transgenic event.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content and composition for example cotton or starch,protein content, oil content and composition, nutritional value,reduction in anti-nutritional compounds, improved processability andbetter storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stresses).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered oil profile characteristics.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered seed shattering characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered seed shattering characteristics andinclude plants such as oilseed rape plants with delayed or reduced seedshattering.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as Tobacco plants, with alteredpost-translational protein modification patterns.

Application Rates

When using the compounds of the formula (I) as fungicides, theapplication rates can be varied within a relatively wide range,depending on the kind of application. The application rate of theinventive active ingredients is

-   -   in the case of treatment of plant parts, for example leaves:        from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more        preferably from 50 to 300 g/ha (in the case of application by        watering or dripping, it is even possible to reduce the        application rate, especially when inert substrates such as        rockwool or perlite are used);    -   in the case of seed treatment: from 0.1 to 200 g per 100 kg of        seed, preferably from 1 to 150 g per 100 kg of seed, more        preferably from 2.5 to 25 g per 100 kg of seed, even more        preferably from 2.5 to 12.5 g per 100 kg of seed;    -   in the case of soil treatment: from 0.1 to 10 000 g/ha,        preferably from 1 to 5000 g/ha.

These application rates are merely by way of example and are notlimiting for the purposes of the invention.

PREPARATION EXAMPLES Preparation of Compounds of Formula (III) Accordingto Process a Preparation of 1-allyl-1H-imidazole-4-carbonitrile

To a solution of 1-H-imidazole-5-carbonitrile (100 g, 1.02 mol) in drydichloromethane (DCM) (3.0 L) at 0° C. was added aqueous NaOH (1 M, 1.23L, 1.23 mmol) followed by tetra-n-butylammonium bromide (32.9 g, 0.102mol). To this biphasic solution was added dropwise allyl bromide (92.7mL, 1.07 mol) and the resulting mixture was stirred at room temperature(21° C.) for 20 h. Thereafter the reaction mixture was diluted withwater (1 L), extracted with dichloromethane (2×1 L), the combinedorganic layers were dried (MgSO₄) and concentrated in vacuo, to provide163 g of a 75:25 mixture of regioisomers (80% purity, 96% yield), whichwere separated by distillation at reduced pressure (0.1-0.2 mbar).

MS (EI): 133 ([M]⁺)

Preparation of Compounds of Formula (I) According to Process BPreparation of cis3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(I-04) and trans3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(1-03) Step 1: Preparation of1-allyl-3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazol-1-ium-4-carbonitriletrifluoromethanesulfonate

[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methanol (0.5 g, 1.8mmol) and 2,6-lutidine (231 μL, 1.98 mmol) were dissolved in DCM (15 mL)under nitrogen. The mixture was cooled to −60° C. andtrifluoromethanesulfonic anhydride (335 μL, 1.98 mmol) was addeddropwise. The mixture was stirred 30 min at −60° C. before addition of1-allylimidazole-4-carbonitrile (0.2 g, 1.5 mmol). After warming to roomtemperature the mixture was stirred for 48 h, concentrated, andrecrystallized from diisopropyl ether to afford the product as a beigesolid (1.17 g) which was used in the next step without furtherpurification.

MS (ESI): 394 ([M-CF₃SO₃ ⁻]⁺)

Step 2: Preparation of cis3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(1-04) and trans3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(1-03)

To a solution of1-allyl-3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazol-1-ium-4-carbonitriletrifluoromethanesulfonate (1.17 g, 2.15 mmol) in DCM (7 mL) was addedmorpholine (0.225 mL, 2.58 mmmol) andtetrakis(triphenylphosphine)palladium (75 mg, 0.064 mmol). The reactionmixture was stirred for 1 h at room temperature. It was then washed withwater. The two layers were separated and the aqueous layer was extractedwith DCM. The combined organic layers were then dried (MgSO₄), filteredand concentrated under reduced pressure. The crude mixture was thenpurified by preparative HPLC to afford trans3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(311 mg, 38%) and cis3-[[3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2-yl]methyl]imidazole-4-carbonitrile(38 mg, 5%).

MS (ESI): 354 ([M+H]⁺)

The following tables illustrate in a non-limiting manner examples ofcompounds according to the invention.

TABLE 1 Compounds according to formula (I) (I)

“Geometric isomer refers to the relative position of the R¹ and R²groups with regards to the oxirane ring” Geometric Ex No R¹ R^(1a) R² R³LogP Isomer I-01 2-chlorophenyl H 4-fluorophenyl chloro 3.19 ^([a])Trans I-02 2-chlorophenyl H 4-fluorophenyl fluoro 2.62 ^([a]) Trans I-032-chlorophenyl H 4-fluorophenyl cyano 3.33 ^([a]) Trans I-042-chlorophenyl H 4-fluorophenyl cyano 2.98 ^([a]) Cis I-052-chlorophenyl H 4-(trifluoromethyl)phenyl cyano 3.96 ^([a]) Trans I-062-chlorophenyl H 4-chlorophenyl cyano 3.68 ^([a]) Trans I-072-chlorophenyl H 4-(trifluoromethoxy)phenyl cyano 4.11 ^([a]) Trans I-082-chlorophenyl H 4-bromophenyl cyano 3.85 ^([a]) Trans I-092-chlorophenyl H 2,4-difluorophenyl cyano 3.06 ^([a]) Trans I-102-fluorophenyl H 4-chlorophenyl cyano 3.41 ^([a]) Trans I-112-bromophenyl H 4-chlorophenyl cyano 3.83 ^([a]) Trans I-122-fluorophenyl H 4-fluorophenyl cyano 3.06 ^([a]) Trans I-132-bromophenyl H 4-fluorophenyl cyano 3.44 ^([a]) Trans I-142-bromophenyl H 4-fluorophenyl fluoro 2.66 ^([a]) Trans I-152-chloropyridin-3-yl H 4-fluorophenyl fluoro 1.57 ^([a]) Cis I-162-chloropyridin-3-yl H 4-fluorophenyl cyano 2.20 ^([a]) Cis I-172-chloropyridin-3-yl H 4-fluorophenyl cyano 2.50 ^([a]) Trans I-182-(trifluoromethyl)- H 4-fluorophenyl cyano 3.49 ^([a]) Trans phenylI-19 2-chlorophenyl H 6-methoxypyridin-3-yl cyano 2.86 ^([a]) Trans I-202-chloropyridin-4-yl H 4-fluorophenyl cyano 2.50 ^([a]) Trans I-213-chlorophenyl H 4-fluorophenyl cyano 3.35 ^([a]) Trans I-222-chlorophenyl H 4-methoxyphenyl cyano 3.26 ^([a]) Trans I-233-bromophenyl H 4-fluorophenyl cyano 3.44 ^([a]) Trans I-244-chlorophenyl H 4-fluorophenyl cyano 3.37 ^([a]) Trans I-252-chlorophenyl H 4-chloro-2-fluorophenyl cyano 3.80 ^([a]) Trans I-262-chlorophenyl H 4-fluoro-2-(trifluoromethyl)- cyano 5.74 ^([a]) Transphenyl I-27 3-(trifluoromethyl)- H 4-fluorophenyl cyano 3.50 ^([a])Trans phenyl I-28 4-(trifluoromethyl)- H 4-fluorophenyl cyano 3.54^([a]) Trans phenyl I-29 2-chlorophenyl H 2-chloro-4-fluorophenyl cyano3.71 ^([a]) Trans LogP values: Measurement of LogP values was performedaccording to EEC directive 79/831 Annex V.A8 by HPLC (High PerformanceLiquid Chromatography) on reversed phase columns with the followingmethods: ^([a]) LogP value is determined by measurement of LC-UV, in anacidic range, with 0.1% formic acid in water and acetonitrile as eluent(linear gradient from 10% acetonitrile to 95% acetonitrile). ^([b]) LogPvalue is determined by measurement of LC-UV, in a neutral range, with0.001 molar ammonium acetate solution in water and acetonitrile aseluent (linear gradient from 10% acetonitrile to 95% acetonitrile).^([c]) LogP value is determined by measurement of LC-UV, in an acidicrange, with 0.1% phosphoric acid and acetonitrile as eluent (lineargradient from 10% acetonitrile to 95% acetonitrile).

If more than one Log P value is available within the same method, allthe values are given and separated by “+”.

Calibration was done with straight-chain alkan2-ones (with 3 to 16carbon atoms) with known Log P values (measurement of Log P values usingretention times with linear interpolation between successive alkanones).Lambda-max-values were determined using UV-spectra from 200 nm to 400 nmand the peak values of the chromatographic signals.

NMR-Peak Lists

1H-NMR data of selected examples are written in form of 1H-NMR-peaklists. To each signal peak are listed the δ-value in ppm and the signalintensity in round brackets. Between the δ-value—signal intensity pairsare semicolons as delimiters.

The peak list of an example has therefore the form:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ;δ_(n) (intensity_(n))

Intensity of sharp signals correlates with the height of the signals ina printed example of a NMR spectrum in cm and shows the real relationsof signal intensities. From broad signals several peaks or the middle ofthe signal and their relative intensity in comparison to the mostintensive signal in the spectrum can be shown.

For calibrating chemical shift for 1H spectra, we use tetramethylsilaneand/or the chemical shift of the solvent used, especially in the case ofspectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilanepeak can occur but not necessarily.

The 1H-NMR peak lists are similar to classical 1H-NMR prints andcontains therefore usually all peaks, which are listed at classicalNMR-interpretation.

Additionally they can show like classical 1H-NMR prints signals ofsolvents, stereoisomers of the target compounds, which are also objectof the invention, and/or peaks of impurities.

To show compound signals in the delta-range of solvents and/or water theusual peaks of solvents, for example peaks of DMSO in DMSO-D₆ and thepeak of water are shown in our 1H-NMR peak lists and have usually onaverage a high intensity.

The peaks of stereoisomers of the target compounds and/or peaks ofimpurities have usually on average a lower intensity than the peaks oftarget compounds (for example with a purity >90%).

Such stereoisomers and/or impurities can be typical for the specificpreparation process. Therefore their peaks can help to recognize thereproduction of our preparation process via“side-products-fingerprints”.

An expert, who calculates the peaks of the target compounds with knownmethods (MestreC, ACD-simulation, but also with empirically evaluatedexpectation values) can isolate the peaks of the target compounds asneeded optionally using additional intensity filters. This isolationwould be similar to relevant peak picking at classical 1H-NMRinterpretation.

Further details of NMR-data description with peak lists you find in thepublication “Citation of NMR Peaklist Data within patent applications”of the Research Disclosure Database Number 564025.

I-01: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.5723 (4.0); 7.5687 (4.4); 7.5681 (4.3); 7.5580 (4.7); 7.5565 (4.0);7.5540 (5.0); 7.4882 (5.0); 7.4854 (4.2); 7.4734 (7.1); 7.4700 (6.8);7.4158 (1.8); 7.4129 (2.3); 7.4010 (5.9); 7.3980 (5.7); 7.3870 (10.3);7.3826 (8.9); 7.3719 (5.6); 7.3672 (11.9); 7.3628 (3.9); 7.3565 (10.3);7.3532 (6.2); 7.3527 (6.2); 7.3494 (9.8); 7.3431 (5.1); 7.3386 (17.2);7.2630 (3.5); 7.0520 (1.1); 7.0461 (8.9); 7.0419 (2.9); 7.0326 (3.6);7.0288 (16.0); 7.0250 (3.4); 7.0156 (2.7); 7.0115 (7.9); 7.0056 (0.9);6.7627 (10.7); 4.4091 (10.2); 4.3789 (11.1); 4.2351 (15.2); 3.7192(11.1); 3.6890 (10.3); 1.2570 (0.6); −0.0002 (4.2)

I-02: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.6932 (0.4); 7.6791 (0.4); 7.6764 (0.4); 7.6692 (0.4); 7.6551 (0.4);7.6525 (0.4); 7.5546 (4.4); 7.5515 (4.8); 7.5398 (5.3); 7.5371 (5.7);7.4992 (0.4); 7.4820 (4.9); 7.4796 (5.0); 7.4671 (6.7); 7.4643 (7.1);7.4431 (0.9); 7.4348 (0.8); 7.4184 (2.9); 7.4160 (3.2); 7.4036 (7.5);7.4009 (7.8); 7.3976 (8.2); 7.3867 (16.0); 7.3824 (12.2); 7.3698 (11.8);7.3565 (2.7); 7.3532 (2.4); 7.2610 (7.5); 7.2505 (0.5); 7.2408 (0.5);7.2312 (0.4); 7.0692 (6.2); 7.0520 (11.6); 7.0348 (5.9); 6.9513 (0.4);6.9230 (8.6); 6.3540 (4.8); 6.3388 (4.9); 5.2929 (0.6); 4.2853 (6.2);4.2552 (6.9); 4.2276 (12.6); 4.1065 (0.6); 3.6505 (8.8); 3.6204 (8.2);1.7445 (2.2); −0.0002 (7.5); −0.0066 (0.5)

I-03: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.6262 (3.9); 7.6229 (4.3); 7.6113 (4.4); 7.6083 (4.8); 7.4958 (4.4);7.4932 (4.4); 7.4806 (6.8); 7.4760 (16.0); 7.4356 (2.6); 7.4270 (13.8);7.4212 (6.3); 7.4089 (5.3); 7.4015 (10.5); 7.3909 (9.2); 7.3890 (9.1);7.3847 (12.0); 7.3782 (4.0); 7.3741 (9.2); 7.2613 (5.9); 7.0993 (0.9);7.0935 (7.4); 7.0896 (2.8); 7.0763 (13.7); 7.0630 (2.5); 7.0592 (6.7);7.0534 (1.0); 5.2945 (0.7); 4.5763 (8.8); 4.5462 (9.5); 4.2535 (14.1);3.8390 (9.3); 3.8089 (8.7); 2.8901 (0.5); −0.0002 (6.0); −0.0065 (0.3)

I-04: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.7728 (3.6); 7.6162 (4.6); 7.2655 (0.3); 7.2272 (2.6); 7.2116 (3.2);7.1596 (3.1); 7.1556 (1.7); 7.1492 (3.6); 7.1422 (4.0); 7.1359 (2.0);7.1318 (3.7); 7.1264 (0.9); 7.1005 (1.3); 7.0967 (1.4); 7.0856 (2.2);7.0823 (2.4); 7.0704 (1.4); 7.0665 (1.5); 7.0143 (1.2); 7.0131 (1.2);6.9988 (3.0); 6.9846 (2.4); 6.9833 (2.4); 6.9764 (3.3); 6.9728 (3.3);6.9610 (1.5); 6.9574 (1.2); 6.8733 (0.6); 6.8681 (3.4); 6.8643 (1.4);6.8509 (6.2); 6.8373 (1.5); 6.8336 (3.2); 5.2919 (16.0); 4.8261 (3.2);4.7957 (4.0); 4.5690 (4.1); 4.5387 (3.3); 4.2264 (5.2); −0.0002 (2.0)

I-05: ¹H-NMR (300.2 MHz, d₆-DMSO):

δ=7.8319 (6.6); 7.8045 (10.6); 7.7397 (10.6); 7.7375 (11.0); 7.7206(10.4); 7.6934 (6.6); 7.6701 (1.3); 7.6592 (7.1); 7.6485 (16.0); 7.6403(8.0); 7.6287 (9.9); 7.6157 (1.8); 7.5451 (1.7); 7.5312 (10.4); 7.5198(6.5); 7.5120 (6.4); 7.5002 (7.3); 5.1911 (5.5); 5.1398 (5.9); 4.3902(13.8); 4.0845 (0.4); 4.0608 (1.1); 4.0371 (1.1); 4.0134 (0.4); 3.8572(5.9); 3.8059 (5.5); 3.3405 (70.9); 2.5333 (7.8); 2.5274 (15.8); 2.5214(21.4); 2.5153 (15.4); 2.5094 (7.2); 2.0944 (1.0); 2.0086 (4.8); 1.2544(1.1); 1.2181 (1.4); 1.1944 (2.8); 1.1706 (1.5); 1.0439 (0.3); 0.0306(0.8); 0.0197 (15.5); 0.0086 (0.8); −0.0411 (4.3)

I-06: ¹H-NMR (300.2 MHz, d₆-DMSO):

δ=7.7389 (5.0); 7.7366 (5.1); 7.6597 (0.4); 7.6488 (2.5); 7.6305 (8.2);7.6186 (3.6); 7.6053 (0.8); 7.5461 (0.5); 7.5349 (0.9); 7.5207 (5.6);7.5108 (3.2); 7.5075 (3.2); 7.5016 (4.0); 7.4929 (15.6); 7.4887 (16.0);7.4681 (0.8); 7.4605 (1.0); 7.4577 (1.0); 5.0915 (2.7); 5.0404 (2.9);4.3326 (6.2); 3.8127 (2.9); 3.7616 (2.7); 3.3420 (10.0); 2.5333 (1.4);2.5273 (2.9); 2.5213 (4.1); 2.5153 (3.0); 2.5093 (1.5); 2.0082 (0.9);1.2536 (0.4); 1.1940 (0.6); 1.0072 (0.5); 0.9858 (0.6); 0.0190 (2.3);−0.0397 (0.4)

I-07: ¹H-NMR (300.2 MHz, d₆-DMSO):

δ=7.7375 (9.5); 7.7349 (9.6); 7.6536 (3.4); 7.6441 (4.2); 7.6350 (6.5);7.6232 (16.0); 7.6163 (6.0); 7.6075 (10.1); 7.6006 (4.0); 7.5851 (4.1);7.5780 (13.3); 7.5689 (1.9); 7.5365 (1.7); 7.5232 (9.4); 7.5119 (5.8);7.5040 (5.9); 7.4922 (6.4); 7.4789 (0.9); 7.4511 (7.5); 7.4245 (5.3);5.1008 (4.8); 5.0496 (5.2); 4.3807 (11.4); 3.8385 (5.2); 3.7875 (4.8);3.3407 (98.8); 2.5334 (6.0); 2.5274 (12.6); 2.5213 (17.1); 2.5152(12.4); 2.5093 (5.8); 0.0305 (0.6); 0.0197 (17.4); 0.0087 (0.7)

I-08: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.6221 (4.1); 7.6195 (4.4); 7.6052 (5.0); 7.5335 (12.1); 7.5167(14.1); 7.4880 (16.0); 7.4771 (7.2); 7.4745 (7.1); 7.4458 (12.9); 7.4378(3.4); 7.4353 (3.3); 7.4225 (5.8); 7.4203 (5.6); 7.4051 (7.8); 7.4013(5.6); 7.3897 (4.8); 7.3864 (4.5); 7.3747 (1.9); 7.3718 (1.7); 7.3012(14.1); 7.2843 (12.5); 7.2603 (9.3); 7.2517 (2.2); 7.2363 (1.5); 7.1792(1.6); 7.1654 (1.4); 7.1541 (0.8); 7.1394 (0.4); 4.6090 (7.4); 4.5788(8.0); 4.2345 (12.8); 3.8234 (7.8); 3.7932 (7.4); 2.3532 (5.2); 1.7242(0.8); −0.0002 (8.7)

I-09: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.8749 (9.2); 7.6499 (10.2); 7.2873 (4.4); 7.2857 (4.6); 7.2713 (5.6);7.2696 (5.7); 7.2608 (28.5); 7.1367 (3.2); 7.1332 (2.8); 7.1210 (7.0);7.1082 (3.7); 7.1052 (4.3); 7.0919 (1.8); 6.9944 (2.4); 6.9933 (2.5);6.9784 (4.9); 6.9642 (2.7); 6.9630 (2.7); 6.8727 (4.3); 6.8700 (4.4);6.8573 (3.5); 6.8545 (3.4); 6.7261 (1.5); 6.7226 (1.7); 6.7102 (2.8);6.7056 (3.2); 6.6931 (1.5); 6.6896 (1.7); 6.6722 (2.1); 6.6674 (1.8);6.6548 (2.5); 6.6514 (3.1); 6.6472 (2.3); 6.6346 (2.1); 6.6298 (1.8);5.1441 (0.3); 5.1390 (0.3); 4.9190 (5.1); 4.8887 (6.1); 4.5789 (6.8);4.5486 (5.8); 4.4043 (11.4); 3.4897 (0.4); 2.9586 (0.8); 2.8844 (0.9);2.4345 (1.2); 2.3548 (0.4); 2.1699 (1.4); 2.0051 (16.0); 1.9948 (0.4);0.0063 (0.8); −0.0002 (21.9); −0.0067 (1.2)

I-10: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.5880 (2.3); 7.5732 (4.8); 7.5585 (2.6); 7.4938 (14.5); 7.4879(14.3); 7.4668 (0.8); 7.4584 (0.4); 7.4434 (1.7); 7.4311 (3.5); 7.4163(3.5); 7.4039 (1.6); 7.3716 (10.5); 7.3547 (16.0); 7.3029 (18.8); 7.2875(12.3); 7.2751 (3.7); 7.2606 (16.7); 7.2537 (4.1); 7.2366 (2.4); 7.2159(2.5); 7.2005 (3.7); 7.1818 (5.1); 7.1639 (3.1); 4.6196 (7.4); 4.5894(8.0); 4.4573 (1.6); 4.4276 (1.7); 4.2747 (13.8); 3.9295 (7.9); 3.8993(7.4); 3.8501 (1.7); 3.8204 (1.6); 2.0426 (0.5); 1.5953 (1.7); 1.2722(0.4); 1.2562 (2.3); 1.2438 (0.6); 1.2283 (0.4); −0.0002 (12.2)

I-11: ¹H-NMR (400.1 MHz, CDCl₃):

δ=8.0273 (0.6); 7.6749 (4.4); 7.6550 (4.9); 7.6261 (3.3); 7.6077 (4.2);7.5106 (10.1); 7.4839 (5.0); 7.4686 (10.6); 7.4180 (3.3); 7.3963 (15.4);7.3866 (16.0); 7.3650 (3.7); 7.3558 (2.9); 7.3359 (3.8); 7.3169 (1.7);7.2723 (19.3); 4.6548 (4.5); 4.6171 (4.9); 4.1783 (9.2); 3.8102 (4.8);3.7725 (4.4); 2.9763 (2.6); 2.8978 (2.5); 1.6670 (9.1); −0.0002 (11.0)

I-12: ¹H-NMR (400.1 MHz, CDCl₃):

δ=7.6062 (2.3); 7.5901 (4.4); 7.5877 (4.4); 7.5719 (2.5); 7.5692 (2.4);7.5150 (16.0); 7.5066 (14.3); 7.4675 (1.2); 7.4635 (1.2); 7.4486 (3.0);7.4295 (3.3); 7.4148 (1.7); 7.4109 (1.5); 7.3509 (6.8); 7.3458 (3.7);7.3380 (7.9); 7.3289 (9.7); 7.3226 (7.0); 7.3162 (8.6); 7.3063 (7.2);7.2859 (4.5); 7.2724 (37.2); 7.2222 (3.6); 7.1983 (4.9); 7.1766 (2.9);7.1082 (7.9); 7.1031 (3.1); 7.0868 (13.6); 7.0700 (3.1); 7.0652 (6.3);4.6177 (7.4); 4.5800 (8.2); 4.4631 (0.4); 4.4262 (0.5); 4.3058 (11.8);3.9409 (8.2); 3.9032 (7.4); 3.8672 (0.5); 3.8305 (0.4); 2.9764 (1.7);2.8978 (1.6); 1.6958 (9.2); 0.0078 (1.5); −0.0002 (21.3)

I-13: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.8319 (0.5); 7.8162 (0.5); 7.6672 (10.1); 7.6515 (10.9); 7.6066(7.8); 7.5922 (9.1); 7.5416 (1.2); 7.5250 (1.2); 7.4797 (5.9); 7.4647(11.1); 7.4504 (14.3); 7.4417 (14.2); 7.3333 (5.8); 7.3184 (8.9); 7.3034(4.7); 7.2619 (14.1); 7.1931 (0.4); 7.1533 (0.6); 7.1393 (0.6); 7.1021(8.8); 7.0860 (15.6); 7.0701 (8.6); 7.0275 (1.0); 7.0113 (0.6); 6.9473(0.3); 6.9320 (0.4); 5.7598 (0.4); 4.7201 (0.6); 4.6359 (2.4); 4.1952(16.0); 3.8670 (2.8); 3.8415 (2.7); 3.7304 (1.8); 3.4996 (0.5); 1.6585(11.9); 1.2561 (0.5); −0.0002 (10.4)

I-14: ¹H-NMR (400.1 MHz, CDCl₃):

δ=7.6655 (0.4); 7.6427 (7.7); 7.6228 (8.4); 7.5343 (5.3); 7.5155 (7.8);7.4520 (5.5); 7.4429 (8.5); 7.4311 (13.4); 7.4217 (10.3); 7.4139 (8.1);7.4088 (9.3); 7.3885 (0.5); 7.3745 (0.4); 7.3048 (4.1); 7.2854 (6.6);7.2667 (3.0); 7.2200 (0.3); 7.0633 (7.7); 7.0420 (14.2); 7.0207 (6.9);6.9819 (0.6); 6.9288 (12.2); 6.3465 (6.5); 6.3274 (6.5); 4.8498 (1.0);4.3209 (8.7); 4.2832 (9.6); 4.1450 (16.0); 3.6284 (9.5); 3.5907 (8.6);2.9336 (0.9); 2.8653 (0.9); −0.0002 (0.8)

I-15: ¹H-NMR (400.1 MHz, CDCl₃):

δ=8.1620 (5.2); 8.1509 (5.4); 8.0048 (3.2); 7.3230 (1.7); 7.3042 (4.9);7.3026 (4.9); 7.2853 (5.7); 7.2051 (1.8); 7.1695 (6.6); 7.1560 (7.7);7.1485 (8.3); 7.1353 (7.1); 7.0681 (0.3); 7.0449 (0.3); 7.0343 (0.3);7.0129 (4.7); 7.0007 (5.0); 6.9942 (4.5); 6.9820 (4.0); 6.9546 (0.4);6.9326 (0.3); 6.8828 (6.1); 6.8617 (11.2); 6.8404 (5.5); 6.6409 (0.3);6.5167 (1.5); 4.8757 (0.5); 4.5749 (5.3); 4.5367 (8.0); 4.4025 (8.3);4.3643 (5.4); 4.2271 (13.4); 2.9521 (16.0); 2.8710 (14.8); −0.0002 (0.8)

I-16: ¹H-NMR (499.9 MHz, CDCl₃):

δ=8.1836 (5.5); 8.1801 (5.9); 8.1741 (5.9); 8.1706 (5.8); 7.7006 (14.9);7.6287 (15.3); 7.3116 (5.2); 7.3082 (5.4); 7.2966 (7.1); 7.2930 (6.0);7.1760 (7.4); 7.1656 (8.2); 7.1588 (9.0); 7.1484 (8.2); 7.0211 (5.5);7.0114 (5.7); 7.0058 (5.4); 6.9962 (5.0); 6.9020 (8.0); 6.8849 (14.4);6.8678 (7.2); 5.3048 (1.0); 4.8479 (8.1); 4.8174 (10.1); 4.6058 (10.2);4.5752 (8.2); 4.2031 (16.0); 1.2578 (0.6); −0.0002 (1.9)

I-17: ¹H-NMR (499.9 MHz, CDCl₃):

δ=8.4904 (4.0); 8.4881 (4.0); 8.4817 (3.8); 8.0424 (2.9); 8.0273 (3.1);8.0183 (3.0); 7.5106 (5.2); 7.4667 (0.6); 7.4487 (3.4); 7.4389 (3.8);7.4339 (3.7); 7.4240 (3.5); 7.4094 (4.7); 7.3988 (5.5); 7.3925 (5.7);7.3822 (5.4); 7.2646 (14.5); 7.1235 (4.8); 7.1065 (8.3); 7.0895 (4.1);4.6569 (3.2); 4.6267 (3.4); 4.2274 (8.3); 4.2084 (0.6); 3.7978 (3.8);3.7676 (3.6); 2.9578 (16.0); 2.8841 (15.0); 1.6443 (1.0); −0.0002 (15.0)

I-18: ¹H-NMR (499.9 MHz, CDCl₃):

δ=8.0186 (0.7); 7.8772 (5.7); 7.8619 (7.0); 7.7799 (6.3); 7.7644 (7.4);7.7365 (3.5); 7.7214 (6.8); 7.7062 (3.8); 7.5713 (3.9); 7.5561 (6.5);7.5411 (3.0); 7.4990 (15.0); 7.4683 (0.4); 7.3995 (12.3); 7.3727 (7.3);7.3688 (5.2); 7.3625 (9.3); 7.3554 (11.0); 7.3492 (6.6); 7.3451 (9.6);7.3200 (0.4); 7.2828 (0.4); 7.2806 (0.4); 7.2616 (32.5); 7.2561 (6.4);7.1080 (1.3); 7.1023 (8.9); 7.0982 (4.9); 7.0852 (16.0); 7.0721 (4.0);7.0679 (8.1); 7.0622 (2.8); 7.0500 (0.3); 4.6008 (8.0); 4.5706 (8.5);4.3735 (9.7); 3.7318 (10.0); 3.7016 (9.5); 2.9576 (4.6); 2.8849 (4.1);1.5797 (15.0); 1.4005 (0.4); 1.3864 (0.9); 1.3722 (0.5); 1.3029 (0.6);1.0203 (0.5); 0.9905 (0.4); 0.9763 (0.8); 0.9623 (0.4); 0.0062 (1.5);−0.0002 (33.9); −0.0064 (7.4)

I-19: ¹H-NMR (499.9 MHz, CDCl₃):

δ=8.2395 (2.2); 8.2362 (2.1); 8.0184 (1.7); 7.6223 (1.5); 7.6194 (1.6);7.6074 (1.7); 7.6053 (1.7); 7.5550 (1.7); 7.5502 (1.6); 7.5378 (1.8);7.5330 (1.7); 7.5130 (3.0); 7.4983 (1.8); 7.4833 (2.3); 7.4806 (2.3);7.4698 (0.4); 7.4526 (2.4); 7.4420 (1.1); 7.4396 (1.1); 7.4270 (2.1);7.4248 (2.0); 7.4101 (2.8); 7.4066 (2.0); 7.3950 (1.6); 7.3915 (1.5);7.3800 (0.6); 7.3768 (0.5); 7.2637 (9.0); 6.7647 (2.6); 6.7476 (2.4);4.5365 (1.8); 4.5063 (1.9); 4.2765 (4.3); 3.9429 (16.0); 3.8608 (2.5);3.8306 (2.3); 2.9573 (12.4); 2.8842 (11.3); 1.6458 (1.3); −0.0002 (9.1)

I-20: ¹H-NMR (499.9 MHz, CDCl₃):

δ=8.5262 (4.2); 8.5161 (4.2); 8.0159 (2.8); 7.5147 (9.1); 7.5080 (12.7);7.4251 (3.6); 7.4150 (3.4); 7.3353 (3.3); 7.3248 (3.8); 7.3184 (4.4);7.3127 (2.3); 7.3082 (3.8); 7.2649 (9.8); 7.1099 (3.7); 7.0928 (6.7);7.0760 (3.3); 4.6452 (3.7); 4.6147 (4.0); 4.1531 (7.8); 3.9405 (4.1);3.9101 (3.8); 2.9577 (16.0); 2.8830 (15.4); 2.5574 (0.4); 1.6315 (3.9);−0.0002 (10.1)

I-21: ¹H-NMR (400.1 MHz, CDCl₃):

δ=8.0265 (2.2); 7.5855 (7.4); 7.5174 (12.9); 7.4677 (0.9); 7.4496 (3.6);7.4342 (16.0); 7.4253 (6.7); 7.4209 (5.5); 7.4132 (2.1); 7.4039 (1.2);7.3970 (0.8); 7.3443 (5.3); 7.3397 (3.3); 7.3315 (6.1); 7.3226 (6.6);7.3148 (3.3); 7.3098 (5.6); 7.2737 (12.3); 7.1081 (5.8); 7.0868 (9.7);7.0653 (4.5); 4.6320 (5.1); 4.5941 (5.6); 4.1904 (11.2); 3.9787 (6.0);3.9408 (5.3); 2.9750 (13.3); 2.8965 (12.4); 1.7180 (8.2); −0.0002 (12.2)

I-22: ¹H-NMR (400.1 MHz, CDCl₃):

δ=7.6378 (1.0); 7.6337 (1.1); 7.6197 (1.2); 7.6154 (1.2); 7.4894 (1.2);7.4812 (3.6); 7.4709 (1.7); 7.4669 (1.8); 7.4384 (0.5); 7.4350 (0.6);7.4199 (1.5); 7.4163 (1.6); 7.4085 (3.2); 7.4021 (1.7); 7.3974 (2.1);7.3920 (1.4); 7.3781 (1.1); 7.3734 (1.1); 7.3592 (0.4); 7.3549 (0.3);7.3354 (0.4); 7.3282 (3.5); 7.3233 (1.3); 7.3113 (1.3); 7.3063 (4.0);7.2993 (0.5); 7.2628 (6.0); 6.9170 (0.5); 6.9098 (3.9); 6.9050 (1.4);6.8928 (1.2); 6.8880 (3.6); 6.8809 (0.5); 4.5671 (2.0); 4.5297 (2.2);4.2558 (3.7); 3.8311 (2.3); 3.8100 (16.0); 3.7937 (2.2); 2.9583 (2.0);2.8850 (1.8); 1.6010 (3.4); −0.0002 (6.3)

I-23: ¹H-NMR (400.1 MHz, CDCl₃):

δ=8.0290 (0.8); 7.6656 (9.6); 7.6429 (0.3); 7.5832 (14.6); 7.5615 (5.9);7.5200 (12.5); 7.4921 (4.8); 7.4732 (6.4); 7.3982 (4.9); 7.3787 (6.8);7.3588 (3.4); 7.3430 (6.4); 7.3298 (7.8); 7.3249 (8.2); 7.3104 (6.4);7.2724 (16.3); 7.1079 (6.8); 7.0870 (11.1); 7.0663 (4.9); 4.6330 (5.8);4.5953 (6.4); 4.1859 (12.6); 3.9769 (6.6); 3.9390 (5.9); 2.9756 (3.4);2.8976 (3.3); 1.6727 (16.0); −0.0002 (16.8)

I-24: ¹H-NMR (400.1 MHz, CDCl₃):

δ=7.5428 (2.9); 7.5223 (3.2); 7.4771 (16.0); 7.3401 (1.3); 7.3272 (1.6);7.3183 (1.8); 7.3054 (1.8); 7.2727 (4.7); 7.1070 (1.6); 7.0856 (2.8);7.0641 (1.4); 4.6089 (1.6); 4.5710 (1.8); 4.1898 (4.0); 3.9615 (1.8);3.9236 (1.6); 2.9752 (1.2); 2.8966 (1.1); 1.6821 (3.1); −0.0002 (4.7)

I-25: ¹H-NMR (400.1 MHz, CDCl₃):

δ=7.6484 (4.0); 7.6433 (4.3); 7.6307 (4.3); 7.6259 (5.0); 7.5590 (0.3);7.5003 (16.0); 7.4803 (6.2); 7.4755 (6.8); 7.4588 (0.5); 7.4400 (2.1);7.4253 (5.6); 7.4215 (5.5); 7.4086 (8.1); 7.4051 (8.2); 7.3876 (13.9);7.3705 (4.0); 7.3502 (6.2); 7.3312 (5.2); 7.3196 (0.6); 7.3108 (0.3);7.2603 (21.4); 7.2500 (7.7); 7.2363 (5.5); 7.2285 (7.7); 7.2161 (9.9);7.2111 (8.9); 7.2071 (8.4); 7.1964 (6.6); 7.1862 (5.6); 7.1815 (5.6);7.1273 (6.2); 7.1230 (5.6); 7.1065 (4.1); 7.1023 (3.8); 4.6818 (6.9);4.6439 (7.5); 4.3100 (14.9); 4.2202 (0.4); 3.9047 (8.6); 3.8668 (7.8);2.9548 (1.4); 2.8828 (1.3); 1.5770 (14.7); −0.0002 (22.1)

I-26: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.7404 (8.7); 7.6868 (13.6); 7.6834 (13.1); 7.6121 (10.5); 7.4791(4.1); 7.4686 (4.6); 7.4624 (4.5); 7.4519 (3.6); 7.3850 (4.0); 7.3813(4.4); 7.3675 (3.5); 7.3641 (3.5); 7.3212 (6.5); 7.3055 (6.7); 7.2835(6.1); 7.2760 (5.0); 7.2679 (5.7); 7.2256 (4.0); 7.2097 (6.4); 7.2011(7.4); 7.1845 (5.2); 7.1259 (4.6); 7.1109 (8.4); 7.0952 (7.1); 7.0803(2.6); 7.0775 (2.4); 6.9669 (3.6); 6.9518 (5.9); 6.9366 (5.1); 6.9268(6.3); 6.9223 (6.9); 6.9175 (7.8); 6.9075 (7.7); 6.8892 (1.9); 6.8775(4.4); 6.8624 (6.6); 6.8473 (4.7); 6.8386 (5.9); 6.8236 (3.8); 6.4868(6.1); 6.4734 (4.8); 5.3122 (3.1); 5.3079 (2.9); 5.2975 (16.0); 5.2899(2.9); 4.8320 (5.6); 4.8017 (7.4); 4.7920 (5.3); 4.7755 (1.7); 4.7607(6.1); 4.6538 (9.4); 4.6485 (14.2); 4.6231 (4.0); 4.4933 (6.8); 4.4629(5.7); 3.9854 (9.7); 2.0032 (0.5); 1.8784 (1.4); −0.0002 (2.2)

I-27: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.7855 (12.7); 7.7651 (7.2); 7.7015 (4.7); 7.6860 (7.9); 7.6524 (5.9);7.6371 (7.4); 7.6218 (2.9); 7.5340 (14.4); 7.4752 (14.5); 7.3681 (7.8);7.3576 (9.1); 7.3510 (9.8); 7.3406 (8.7); 7.2926 (0.9); 7.0845 (8.2);7.0674 (14.5); 7.0503 (7.5); 5.2859 (0.9); 4.6334 (8.5); 4.6029 (9.2);4.2627 (16.0); 3.9442 (9.1); 3.9138 (8.4); 1.9980 (0.6); −0.0002 (0.4)

I-28: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.7621 (10.6); 7.7457 (16.0); 7.6904 (15.3); 7.6740 (10.3); 7.5170(14.8); 7.4902 (15.0); 7.3560 (7.6); 7.3456 (8.6); 7.3430 (7.3); 7.3387(9.9); 7.3284 (9.0); 7.2820 (1.3); 7.0934 (8.5); 7.0764 (15.1); 7.0592(7.8); 5.2910 (1.9); 4.6079 (9.3); 4.5775 (10.1); 4.2611 (14.8); 3.9463(9.4); 3.9158 (8.7); −0.0002 (0.9)

I-29: ¹H-NMR (499.9 MHz, CDCl₃):

δ=7.6718 (4.2); 7.6574 (4.6); 7.5028 (5.1); 7.5011 (5.1); 7.4897 (10.8);7.4458 (2.0); 7.4326 (5.1); 7.4144 (5.6); 7.4099 (4.4); 7.3976 (4.2);7.3949 (4.0); 7.3826 (1.5); 7.3422 (5.5); 7.2810 (1.0); 7.2269 (5.0);7.2225 (6.6); 7.2105 (7.2); 7.2059 (7.4); 7.1933 (2.9); 6.9430 (2.2);6.9384 (2.2); 6.9266 (3.8); 6.9225 (3.8); 6.9101 (2.0); 6.9056 (1.9);5.2947 (16.0); 4.7458 (1.7); 4.7158 (1.8); 4.4337 (12.6); 4.0793 (2.5);4.0490 (2.4); 2.0019 (0.8); −0.0002 (0.7)

BIOLOGICAL EXAMPLES Example A: In Vivo Preventive Test on Pucciniarecondita (Brown Rust on Wheat)

Solvent:  5% by volume of Dimethyl sulfoxide 10% by volume of AcetoneEmulsifier: 1 μl of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture ofDimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to thedesired concentration.

The young plants of wheat are treated by spraying the active ingredientprepared as described above. Control plants are treated only with anaqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Puccinia recondita spores. The contaminatedwheat plants are incubated for 24 hours at 20° C. and at 100% relativehumidity and then for 10 days at 20° C. and at 70-80% relative humidity.

The test is evaluated 11 days after the inoculation. 0% means anefficacy which corresponds to that of the control plants while anefficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 500 ppm of activeingredient: I-01; I-02; I-05; I-06; I-07; I-10; I-11; I-12; I-13; I-18;I-19; I-20; I-21; I-22; I-23; I-24; I-25; I-28; I-29.

Example B: In Vivo Preventive Test on Septoria tritici (Leaf Spot onWheat)

Solvent:  5% by volume of Dimethyl sulfoxide 10% by volume of AcetoneEmulsifier: 1 μl of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture ofDimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to thedesired concentration.

The young plants of wheat are treated by spraying the active ingredientprepared as described above. Control plants are treated only with anaqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Septoria tritici spores. The contaminated wheatplants are incubated for 72 hours at 18° C. and at 100% relativehumidity and then for 21 days at 20° C. and at 90% relative humidity.

The test is evaluated 24 days after the inoculation. 0% means anefficacy which corresponds to that of the control plants while anefficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 80% and 89% at a concentration of 500 ppm of activeingredient: 1-04; I-21.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 500 ppm of activeingredient: I-01; I-02; I-03; I-05; I-06; I-07; I-08; I-09; I-10; I-11;I-12; I-13; I-14; I-17; I-18; I-19; I-20; I-22; I-23; I-24; I-25; I-27;I-28; I-29.

Example C: In Vivo Preventive Test on Sphaerotheca fuliginea (PowderyMildew on Cucurbits)

Solvent:  5% by volume of Dimethyl sulfoxide 10% by volume of AcetoneEmulsifier: 1 μl of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture ofDimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to thedesired concentration.

The young plants of gherkin are treated by spraying the activeingredient prepared as described above. Control plants are treated onlywith an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Sphaerotheca fuidiginea spores. Thecontaminated gherkin plants are incubated for 72 hours at 18° C. and at100% relative humidity and then for 12 days at 20° C. and at 70-80%relative humidity.

The test is evaluated 15 days after the inoculation. 0% means anefficacy which corresponds to that of the control plants while anefficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 500 ppm of activeingredient: I-01; I-02; I-03; I-04; I-05; I-06; I-07; I-08; I-09; I-10;I-12; I-14; I-15; I-16; I-17; I-18; I-19; I-20; I-21; I-22; I-23; I-24;I-25; I-26; I-27; I-28; I-29.

Example D: In Vivo Preventive Test on Uromyces appendiculatus (BeanRust)

Solvent:  5% by volume of Dimethyl sulfoxide 10% by volume of AcetoneEmulsifier: 1 μl of Tween ® 80 per mg of active ingredient

The active ingredients are made soluble and homogenized in a mixture ofDimethyl sulfoxide/Acetone/Tween® 80 and then diluted in water to thedesired concentration.

The young plants of bean are treated by spraying the active ingredientprepared as described above. Control plants are treated only with anaqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

After 24 hours, the plants are contaminated by spraying the leaves withan aqueous suspension of Uromyces appendiculatus spores. Thecontaminated bean plants are incubated for 24 hours at 20° C. and at100% relative humidity and then for 10 days at 20° C. and at 70-80%relative humidity.

The test is evaluated 11 days after the inoculation. 0% means anefficacy which corresponds to that of the control plants while anefficacy of 100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 80% and 89% at a concentration of 500 ppm of activeingredient: 1-04; I-19.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 500 ppm of activeingredient: I-01; I-02; I-03; I-05; I-06; I-07; I-08; I-09; I-10; I-11;I-12; I-13; I-14; I-17; I-18; I-20; I-21; I-22; I-23; I-24; I-25; I-27;I-28; I-29.

Example E: In Vivo Preventive Test on Phakopsora Test (Soybeans)

Solvent: 24.5 parts by weight of acetone 24.5 parts by weight ofdimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycolether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the causal agent of soybean rust (Phakopsorapachyrhizi) and stay for 24 h without light in an incubation cabinet atapproximately 24° C. and a relative atmospheric humidity of 95%.

The plants remain in the incubation cabinet at approximately 24° C. anda relative atmospheric humidity of approximately 80% and a day/nightinterval of 12 h.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 80% and 89% at a concentration of 10 ppm of activeingredient: 1-02; 1-03; 1-08; 1-12; 1-18.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 10 ppm of activeingredient: 1-06; 1-07; I-21.

Example F: In Vivo Preventive Blumeria Test (Barley)

Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier:  1 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application.

After the spray coating has been dried, the plants are dusted withspores of Blumeria graminis fsp. hordei.

The plants are placed in the greenhouse at a temperature ofapproximately 18° C. and a relative atmospheric humidity ofapproximately 80% to promote the development of mildew pustules.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed.

In this test the following compounds according to the invention showedefficacy between 80% and 89% at a concentration of 500 ppm of activeingredient: I-11.

In this test the following compounds according to the invention showedefficacy between 90% and 100% at a concentration of 500 ppm of activeingredient: I-01; I-02; I-03; I-05; I-06; I-07; I-10; I-12; I-13; I-14;I-25; I-29.

1. Imidazole derivative of formula (I)

wherein R¹ and R^(1a) independently from each other represent hydrogen,C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen, C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl, optionally halogen,C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted bicycloalkyl, optionallyhalogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedC₃-C₇-cycloalkyl-C₁-C₄-alkyl, optionally C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-halocycloalkyl-C₁-C₄-alkyl, optionallyC₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedC₃-C₇-halocycloalkyl-C₁-C₄-haloalkyl, optionally C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₁-C₄-haloalkyl, optionallyhalogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedC₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl, naphthyl, 5-membered heteroaryl, or asubstituent of formula Q¹, wherein the naphthyl, and 5-memberedheteroaryl is non-substituted or substituted by one or more group(s)selected from halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,C₁-C₈-haloalkyl having 1 to 5 halogen atoms, C₃-C₈-cycloalkyl,C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms,C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having1 to 5 halogen atoms, C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfonyl,tri(C₁-C₈-alkyl)-silyloxy, tri(C₁-C₈-alkyl)-silyl, aryl, aryloxy,heteroaryl, heteroaryloxy, wherein the aryl, aryloxy, heteroaryl,heteroaryloxy is non-substituted or substituted by one or more group(s)selected from halogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl,C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, benzyl, phenyl, 5-membered heteroaryl,δ-membered heteroaryl, δ-membered heteroaryloxy, benzyloxy, orphenyloxy, wherein the benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, δ-membered heteroaryloxy, benzyloxy, or phenyloxy isnon-substituted or substituted by one or more group(s) selected fromhalogen, nitro, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and wherein Q¹ represents aδ-membered aromatic cycle of formula (Q¹-I)

wherein U¹ represents CX¹ or N; U² represents CX² or N; U³ representsCX³ or N; U⁴ represents CX⁴ or N; U⁵ represents CX⁵ or N; wherein X¹,X², X³, X⁴, and X⁵ independently from each other represent hydrogen,halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkylhaving 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkylhaving 1 to 5 halogen atoms, C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl,C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to 5 halogen atoms,C₃-C₆-cycloalkoxy, C₁-C₈-alkyl-sulfonyl, tri(C₁-C₈-alkyl)-silyloxy,tri(C₁-C₈-alkyl)-silyl, aryl, aryloxy, heteroaryl, heteroaryloxy,wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is non-substitutedor substituted by one or more group(s) selected from halogen,pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy,C₁-C₈-haloalkyloxy, tri(C₁-C₈-alkyl)silyl,tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfonyl,C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, benzyl, phenyl, 5-membered heteroaryl,δ-membered heteroaryl, δ-membered heteroaryloxy, benzyloxy, orphenyloxy, wherein the benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, δ-membered heteroaryloxy, benzyloxy, or phenyloxy isnon-substituted or substituted by one or more group(s) selected fromhalogen, nitro, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and wherein at most two ofU¹, U², U³, U⁴ and U⁵ can represent N; or U¹ and U² or U² and U³ or U³and U⁴ form together an additional saturated or unsaturated 4 toδ-membered halogen- or C₁-C₈-alkyl-substituted or non-substituted ring;R² represents C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen,C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl,optionally halogen, C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedbicycloalkyl, optionally halogen, C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₁-C₄-alkyl, optionallyC₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedC₃-C₇-halocycloalkyl-C₁-C₄-alkyl, optionally C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-halocycloalkyl-C₁-C₄-haloalkyl,optionally C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substitutedC₃-C₇-cycloalkyl-C₁-C₄-haloalkyl, optionally halogen, C₁-C₄-alkyl-, orC₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl, naphthyl,5-membered heteroaryl, or a substituent of formula Q², wherein thenaphthyl, and 5-membered heteroaryl is non-substituted or substituted byone or more group(s) selected from halogen, nitro,pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 5halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl having 1 to 5halogen atoms, C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy,C₁-C₈-haloalkoxy having 1 to 5 halogen atoms, C₃-C₆-cycloalkoxy,C₁-C₈-alkylsulfonyl, tri(C₁-C₈-alkyl)-silyloxy, tri(C₁-C₈-alkyl)-silyl,aryl, aryloxy, heteroaryl, heteroaryloxy, wherein the aryl, aryloxy,heteroaryl, heteroaryloxy is non-substituted or substituted by one ormore group(s) selected from halogen, pentafluoro-λ⁶-sulfanyl,C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy,C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, benzyl, phenyl, 5-membered heteroaryl,δ-membered heteroaryl, δ-membered heteroaryloxy, benzyloxy, orphenyloxy, wherein the benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, δ-membered heteroaryloxy, benzyloxy, or phenyloxy isnon-substituted or substituted by one or more group(s) selected fromhalogen, nitro, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and wherein Q² represents aδ-membered aromatic cycle of formula (Q²-I)

wherein Z¹ represents CY¹ or N; Z² represents CY² or N; Z³ representsCY³ or N; Z⁴ represents CY⁴ or N; Z⁵ represents CY⁵ or N; wherein Y¹,Y², Y³ Y⁴, and Y⁵ independently from each other represent hydrogen,halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkylhaving 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkylhaving 1 to 5 halogen atoms, C₁-C₈-haloalkyl-C₃-C₇-cycloalkyl,C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to 5 halogen atoms,C₃-C₆-cycloalkoxy, C₁-C₈-alkyl-sulfonyl, tri(C₁-C₈-alkyl)-silyloxy,tri(C₁-C₈-alkyl)-silyl, aryl, aryloxy, heteroaryl, heteroaryloxy,wherein the aryl, aryloxy, heteroaryl, heteroaryloxy is non-substitutedor substituted by one or more group(s) selected from halogen,pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy,C₁-C₈-haloalkyloxy, tri(C₁-C₈-alkyl)silyl,tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl, C₃-C₇-cycloalkyl,C₃-C₇-halocycloalkyl, C₃-C₆-cycloalkoxy, C₁-C₈-alkylsulfonyl,C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, benzyl, phenyl, 5-membered heteroaryl,δ-membered heteroaryl, δ-membered heteroaryloxy, benzyloxy, orphenyloxy, wherein the benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, δ-membered heteroaryloxy, benzyloxy, or phenyloxy isnon-substituted or substituted by one or more group(s) selected fromhalogen, nitro, C₁-C₈-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy or pentafluoro-λ⁶-sulfanyl; and wherein at most two ofZ¹, Z², Z³, Z⁴ and Z⁵ can represent N; or Z¹ and Z² or Z² and Z³ or Z³and Z⁴ form together an additional saturated or unsaturated 4 toδ-membered halogen- or C₁-C₈-alkyl-substituted or non-substituted ring;R³ represents halogen, hydroxyl, cyano, isocyano, amino, sulfanyl,pentafluoro-λ⁶-sulfanyl, carboxaldehyde, hydroxycarbonyl, C₁-C₈-alkyl,C₁-C₈-haloalkyl, C₁-C₈-cyanoalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₇-cycloalkenyl,C₃-C₇-halocycloalkenyl, C₄-C₁₀-cycloalkylalkyl,C₄-C₁₀-halocycloalkylalkyl, C₆-C₁₂-cycloalkylcycloalkyl,C₁-C₈-alkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy-C₃-C₇-cycloalkyl,tri(C₁-C₈-alkyl)silyl-C₃-C₇-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,C₂-C₈-alkenyloxy, C₂-C₈-haloalkenyloxy, C₃-C₈-alkynyloxy,C₃-C₈-haloalkynyloxy, C₁-C₈-alkylamino, C₁-C₈-haloalkylamino,C₁-C₈-cyanoalkoxy, C₄-C₈-cycloalkylalkoxy, C₃-C₆-cycloalkoxy,C₁-C₈-alkylsulfanyl, C₁-C₈-haloalkylsulfanyl, C₁-C₈-alkylcarbonyl,C₁-C₈-haloalkylcarbonyl, arylcarbonyl, aryl-C₁-C₆-alkylcarbonyl,C₃-C₈-cycloalkylcarbonyl, C₃-C₈-halocycloalkylcarbonyl,C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl,N—C₁-C₈-alkyloxycarbamoyl, C₁-C₈-alkoxycarbamoyl,N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aminothiocarbonyl,C₁-C₈-alkoxycarbonyl, C₁-C₈-haloalkoxycarbonyl,C₃-C₈-cycloalkoxycarbonyl, C₂-C₈-alkoxyalkylcarbonyl,C₂-C₈-haloalkoxyalkylcarbonyl, C₃-C₁₀-cycloalkoxyalkylcarbonyl,C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl,C₃-C₈-cycloalkylaminocarbonyl, C₁-C₈-alkylcarbonyloxy,C₁-C₈-haloalkylcarbonyloxy, C₃-C₈-cycloalkylcarbonyloxy,C₁-C₈-alkylcarbonylamino, C₁-C₈-haloalkylcarbonylamino,C₁-C₅-alkylaminocarbonyloxy, di-C₁-C₈-alkylaminocarbonyloxy,C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl,C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, C₁-C₈-alkylaminosulfamoyl,di-C₁-C₈-alkylaminosulfamoyl, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,(C₃-C₇-cycloalkoxyimino)-C₁-C₈-alkyl, hydroxyimino-C₁-C₈-alkyl,(C₁-C₈-alkoxyimino)-C₃-C₇-cycloalkyl, hydroxyimino-C₃-C₇-cycloalkyl,(C₁-C₈-alkylimino)-oxy, (C₁-C₈-alkylimino)-oxy-C₁-C₈-alkyl,(C₃-C₇-cycloalkylimino)-oxy-C₁-C₈-alkyl,(C₁-C₆-alkylimino)-oxy-C₃-C₇-cycloalkyl,(C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,(C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, (benzyloxyimino)-C₁-C₈-alkyl,C₁-C₈-alkoxyalkyl, C₁-C₈-alkylthioalkyl, C₁-C₈-alkoxyalkoxyalkyl,C₁-C₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino,phenylsulfanyl, or phenylamino, wherein the benzyl, phenyl, 5-memberedheteroaryl, δ-membered heteroaryl, benzyloxy or phenyloxy isnon-substituted or substituted by one or more group(s) selected fromhalogen, hydroxyl, cyano, isocyano, amino, sulfanyl,pentafluoro-λ⁶-sulfanyl, carboxaldehyde, hydroxycarbonyl, C₁-C₈-alkyl,C₁-C₈-haloalkyl, C₁-C₈-cyanoalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy,tri(C₁-C₈-alkyl)silyl, tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl,C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₃-C₇-cycloalkenyl,C₃-C₇-halocycloalkenyl, C₄-C₁₀-cycloalkylalkyl,C₄-C₁₀-halocycloalkylalkyl, C₆-C₁₂-cycloalkylcycloalkyl,C₁-C₈-alkyl-C₃-C₇-cycloalkyl, C₁-C₈-alkoxy-C₃-C₇-cycloalkyl,tri(C₁-C₈-alkyl)silyl-C₃-C₇-cycloalkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,C₂-C₈-alkenyloxy, C₂-C₈-haloalkenyloxy, C₃-C₈-alkynyloxy,C₃-C₈-haloalkynyloxy, C₁-C₈-alkylamino, C₁-C₈-haloalkylamino,C₁-C₈-cyanoalkoxy, C₄-C₈-cycloalkylalkoxy, C₃-C₆-cycloalkoxy,C₁-C₈-alkylsulfanyl, C₁-C₈-haloalkylsulfanyl, C₁-C₈-alkylcarbonyl,C₁-C₈-haloalkylcarbonyl, arylcarbonyl, aryl-C₁-C₆-alkylcarbonyl,C₃-C₈-cycloalkylcarbonyl, C₃-C₈-halocycloalkylcarbonyl,C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl,N—C₁-C₈-alkyloxycarbamoyl, C₁-C₈-alkoxycarbamoyl,N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aminothiocarbonyl,C₁-C₈-alkoxycarbonyl, C₁-C₈-haloalkoxycarbonyl,C₃-C₈-cycloalkoxycarbonyl, C₂-C₈-alkoxyalkylcarbonyl,C₂-C₈-haloalkoxyalkylcarbonyl, C₃-C₁₀-cycloalkoxyalkylcarbonyl,C₁-C₈-alkylaminocarbonyl, di-C₁-C₈-alkylaminocarbonyl,C₃-C₈-cycloalkylaminocarbonyl, C₁-C₈-alkylcarbonyloxy,C₁-C₈-haloalkylcarbonyloxy, C₃-C₅-cycloalkylcarbonyloxy,C₁-C₈-alkylcarbonylamino, C₁-C₈-haloalkylcarbonylamino,C₁-C₈-alkylaminocarbonyloxy, di-C₁-C₈-alkylaminocarbonyloxy,C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulfinyl, C₁-C₈-haloalkylsulfinyl,C₁-C₈-alkylsulfonyl, C₁-C₈-haloalkylsulfonyl, C₁-C₈-alkylsulfonyloxy,C₁-C₈-haloalkylsulfonyloxy, C₁-C₈-alkylaminosulfamoyl,di-C₁-C₈-alkylaminosulfamoyl, (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl,(C₃-C₇-cycloalkoxyimino)-C₁-C₈-alkyl, hydroxyimino-C₁-C₈-alkyl,(C₁-C₈-alkoxyimino)-C₃-C₇-cycloalkyl, hydroxyimino-C₃-C₇-cycloalkyl,(C₁-C₈-alkylimino)-oxy, (C₁-C₈-alkylimino)-oxy-C₁-C₈-alkyl,(C₃-C₇-cycloalkylimino)-oxy-C₁-C₈-alkyl,(C₁-C₆-alkylimino)-oxy-C₃-C₇-cycloalkyl,(C₁-C₈-alkenyloxyimino)-C₁-C₈-alkyl,(C₁-C₈-alkynyloxyimino)-C₁-C₈-alkyl, (benzyloxyimino)-C₁-C₈-alkyl,C₁-C₈-alkoxyalkyl, C₁-C₈-alkylthioalkyl, C₁-C₈-alkoxyalkoxyalkyl,C₁-C₈-haloalkoxyalkyl, benzyl, phenyl, 5-membered heteroaryl, δ-memberedheteroaryl, benzyloxy, phenyloxy, benzylsulfanyl, benzylamino,phenylsulfanyl, or phenylamino; And/or a salt and/or N-oxide thereof. 2.Imidazole derivative of formula (I) according to claim 1, wherein R¹represents hydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen-,C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl, naphthyl,thiazolyl, thienyl or a substituent of formula Q¹, wherein the naphthyl,thiazolyl, or thienyl is non-substituted or substituted by one or moregroup(s) selected from halogen, nitro, pentafluoro-λ⁶-sulfanyl,C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 5 halogen atoms,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms,C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to 5 halogen atoms; and whereinQ¹ represents a δ-membered aromatic cycle of formula (Q¹-I)

And/or a salt and/or N-oxide thereof.
 3. Imidazole derivative of formula(I) according to claim 1, wherein R¹ represents a substituent of formulaQ¹, wherein Q¹ represents a δ-membered aromatic cycle of formula (Q¹-I)

wherein U¹ represents CX¹ or N; U² represents CX² or N; U³ representsCX³ or N; U⁴ represents CX⁴ or N; U⁵ represents CX⁵ or N; wherein X¹,X², X³, X⁴ and X⁵ represent independently from each other hydrogen,halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkylhaving 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkylhaving 1 to 5 halogen atoms, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to5 halogen atoms, aryl, aryloxy, heteroaryl, heteroaryloxy, wherein thearyl, aryloxy, heteroaryl, heteroaryloxy is non-substituted orsubstituted or substituted by one or more group(s) selected fromhalogen, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl,C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy, optionally represent independentlyfrom each other hydrogen, fluorine, chlorine, bromine, ortrifluoromethyl, And/or a salt and/or N-oxide thereof.
 4. Imidazolederivative of formula (I) according to claim 1, wherein R^(1a)represents hydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen-,C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl,optionally hydrogen, And/or a salt and/or N-oxide thereof.
 5. Imidazolederivative of formula (I) according to claim 1, wherein R² representshydrogen, C₁-C₈-alkyl, C₁-C₈-haloalkyl, optionally halogen-,C₁-C₄-alkyl-, or C₁-C₄-haloalkyl-substituted C₃-C₇-cycloalkyl, naphthyl,thiazolyl, thienyl or a substituent of formula Q², wherein the naphthyl,thiazolyl, or thienyl is non-substituted or substituted by one or moregroup(s) selected from halogen, nitro, pentafluoro-λ⁶-sulfanyl,C₁-C₈-alkyl, C₁-C₈-haloalkyl having 1 to 5 halogen atoms,C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkyl having 1 to 5 halogen atoms,C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to 5 halogen atoms; and whereinQ² represents a δ-membered aromatic cycle of formula (Q²-I)

And/or a salt and/or N-oxide thereof.
 6. Imidazole derivative of formula(I) according to claim 1, wherein R² represents a substituent of formulaQ², wherein Q² represents a δ-membered aromatic cycle of formula (Q²-I)

wherein Z¹ represents CY¹ or N; Z² represents CY² or N; Z³ representsCY³ or N; Z⁴ represents CY⁴ or N; Z⁵ represents CY⁵ or N; wherein Y¹,Y², Y³ Y⁴ and Y⁵ represent independently from each other hydrogen,halogen, nitro, pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkylhaving 1 to 5 halogen atoms, C₃-C₈-cycloalkyl, C₃-C₈-halocycloalkylhaving 1 to 5 halogen atoms, C₁-C₈-alkoxy, C₁-C₈-haloalkoxy having 1 to5 halogen atoms, aryl, aryloxy, heteroaryl, heteroaryloxy, wherein thearyl, aryloxy, heteroaryl, heteroaryloxy is non-substituted orsubstituted by one or more group(s) selected from halogen,pentafluoro-λ⁶-sulfanyl, C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy,C₁-C₈-haloalkyloxy, optionally represent independently from each otherhydrogen, fluorine, chlorine, bromine, trifluoromethyl, methoxy ortrifluoromethoxy, And/or a salt and/or N-oxide thereof.
 7. Imidazolederivative of formula (I) according to claim 1, wherein R³ representshalogen, cyano, carboxaldehyde, hydroxycarbonyl, C₂-C₄-alkyl,C₁-C₄-haloalkyl, C₁-C₄-cyanoalkyl, C₁-C₄-alkyloxy, C₁-C₄-haloalkyloxy,C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₂-C₅-alkenyl, C₂-C₅-alkynyl,C₁-C₄-alkylsulfanyl, C₁-C₄-haloalkylsulfanyl, C₁-C₄-alkylcarbonyl,C₁-C₄-haloalkylcarbonyl, aminothiocarbonyl, C₁-C₄-alkoxycarbonyl,C₁-C₄-haloalkoxycarbonyl, benzyl, phenyl, furyl, pyrrolyl, thienyl,pyridyl, benzyloxy, or phenyloxy, wherein the benzyl, phenyl, 5-memberedheteroaryl, δ-membered heteroaryl, benzyloxy or phenyloxy may beoptionally substituted by one or more group(s) selected from halogen,C₁-C₈-alkyl, C₁-C₈-haloalkyl, C₁-C₈-alkyloxy, C₁-C₈-haloalkyloxy;optionally represents fluorine, chlorine, bromine, iodine, cyano,hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl, methoxy,methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl (acetyl), carboxyl,aminothiocarbonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, or2-thienyl, more preferred fluorine, chlorine, bromine, iodine, or cyano,And/or a salt and/or N-oxide thereof.
 8. Imidazole derivative of formula(I) according to claim 1, wherein the imidazole derivative of formula(I) is represented by formula (I-1-Q-I-1)

wherein R³ represents fluorine, chlorine, bromine, iodine, cyano,hydroxycarbonyl, carboxaldehyde, trifluoromethyl, cyanomethyl, methoxy,methylsulfanyl, cyclopropyl, ethinyl, methylcarbonyl (acetyl), carboxyl,aminothiocarbonyl, methoxycarbonyl, ethoxycarbonyl, phenyl, or2-thienyl, optionally fluorine, chlorine, bromine, cyano, ortrifluoromethyl, optionally fluorine, chlorine, or cyano; X¹ representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,trifluoromethyl, methoxy, trifluoromethoxy, or chlorodifluoromethoxy,optionally represents hydrogen, fluorine, chlorine, bromine ortrifluoromethyl; X² represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,trifluoromethoxy, or chlorodifluoromethoxy, optionally representshydrogen; X³ represents hydrogen, fluorine, chlorine, bromine,pentafluoro-λ⁶-sulfanyl, methyl, ethyl, n-propyl, isopropyl, n-, iso-,sec-, tert-butyl, difluoromethyl, trifluoromethyl, cyclopropyl,fluorocyclopropyl, chlorocyclopropyl, methoxy, trifluoromethoxy,chlorodifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, phenyloxy andpyridin-3-yloxy, wherein the phenyloxy and pyridin-3-yloxy isnon-substituted or substituted by one or more group(s) selected fromfluorine, chlorine, bromine, iodine, pentafluoro-λ⁶-sulfanyl,difluoromethyl, trifluoromethyl, optionally represents hydrogen,fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy,trifluoromethoxy, or chlorodifluoromethoxy, optionally representshydrogen, fluorine, chlorine, bromine or trifluoromethyl; X⁴ representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,trifluoromethyl, methoxy, trifluoromethoxy, or chlorodifluoromethoxy,optionally represents hydrogen, fluorine, chlorine, bromine ortrifluoromethyl; X⁵ represents hydrogen, fluorine, chlorine, bromine,methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,trifluoromethoxy, or chlorodifluoromethoxy, optionally representshydrogen, fluorine, chlorine, bromine or trifluoromethyl; Y¹ representshydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl,trifluoromethyl, methoxy, trifluoromethoxy, or chlorodifluoromethoxy,optionally represents hydrogen, fluorine, chlorine, or bromine; Y²represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, orchlorodifluoromethoxy, optionally represents hydrogen; Y³ representshydrogen, fluorine, chlorine, bromine, pentafluoro-λ⁶-sulfanyl, methyl,ethyl, n-propyl, isopropyl, n-, iso-, sec-, tert-butyl, difluoromethyl,trifluoromethyl, cyclopropyl, fluorocyclopropyl, chlorocyclopropyl,methoxy, trifluoromethoxy, chlorodifluoromethoxy,1,1,2,2-tetrafluoroethoxy, phenyloxy and pyridin-3-yloxy, wherein thephenyloxy and pyridin-3-yloxy is non-substituted or substituted by oneor more group(s) selected from fluorine, chlorine, bromine, iodine,pentafluoro-λ⁶-sulfanyl, difluoromethyl, trifluoromethyl, optionallyrepresents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl, methoxy, trifluoromethoxy, or chlorodifluoromethoxy,optionally represents fluorine, chlorine, bromine, trifluoromethyl,methoxy, or trifluoromethoxy; Y⁴ represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl,methoxy, trifluoromethoxy, or chlorodifluoromethoxy, optionallyrepresents hydrogen; and Y⁵ represents hydrogen, fluorine, chlorine,bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, methoxy,trifluoromethoxy, or chlorodifluoromethoxy, optionally representshydrogen, fluorine, chlorine, or bromine, And/or a salt and/or N-oxidethereof.
 9. Composition for controlling one or more harmfulmicroorganisms, optionally for controlling phytopathogenic harmfulfungi, comprising a content of at least one compound of formula (I)and/or a salt and/or N-oxide thereof according to claim 1, in additionto at least one extender and/or surfactant.
 10. Composition according toclaim 9 comprising at least one further active ingredient selected fromthe group of insecticides, attractants, sterilants, bactericides,acaricides, nematicides, fungicides, growth regulators, herbicides,fertilizers, safeners and semiochemicals.
 11. Process for producing acomposition for controlling one or more harmful microorganisms,optionally for controlling phytopathogenic harmful fungi, comprisingmixing at least one compound of formula (I) and/or a salt and/or N-oxidethereof according to claim 1, with at least one extender and/orsurfactant.
 12. Method for controlling one or more harmfulmicroorganisms, optionally phytopathogenic harmful fungi, in cropprotection and/or in protection of materials, comprising applying atleast one compound of formula (I)) and/or a salt and/or N-oxide thereofaccording to claim 1, to the harmful microorganisms and/or a habitatthereof.
 13. A product comprising at least one compound of formula (I))and/or a salt and/or N-oxide thereof according to claim 1, for controlof one or more harmful microorganisms, optionally phytopathogenicharmful fungi, in crop protection and/or in protection of materials. 14.A product comprising at least one compound of formula (I)) and/or a saltand/or N-oxide thereof according to claim 1, for treatment of atransgenic plant.
 15. A product comprising at least one compound offormula (I)) and/or a salt and/or N-oxide thereof according to claim 1,for treatment of seed, optionally seed of a transgenic plant.